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Journal articles on the topic 'Methyl chloroformate'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Andraos, John. "A green metrics assessment of phosgene and phosgene-free syntheses of industrially important commodity chemicals." Pure and Applied Chemistry 84, no. 3 (2011): 827–60. http://dx.doi.org/10.1351/pac-con-11-06-12.

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Synthesis plans for the following important industrial commodity chemicals using phosgene and phosgene-free chemistries have been analyzed and compared by green metrics to determine the most material-efficient routes so far developed (number of plans given in parentheses): dimethyl carbonate (DMC) (31), diphenyl carbonate (DPC) (40), diphenylurea (DPU) (23), methyl carbamate (MC) (8), methyl chloroformate (MCF) (6), methyl N-phenylcarbamate (MNPC) (25), methyl phenyl carbonate (MPC) (32), phenyl isocyanate (PI) (19), phenyl chloroformate (PCF) (10), and urea (13). Implications of these results

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2

Jadhav, Vinod H., Shubhada S. Deshpande, Hanumant B. Borate, and Radhika D. Wakharkar. "Microwave Promoted Solvent-free One-pot Synthesis of N,N′-disubstituted Urea Derivatives." Journal of Chemical Research 2005, no. 3 (2005): 205–8. http://dx.doi.org/10.3184/0308234054213753.

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An efficient one-pot synthesis of N,N′-disubstituted urea derivatives from substituted anilines, ethyl chloroformate and methyl anthranilate or methyl 3-amino-2-butenoate under microwave irradiation is reported.

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3

Patroni, JJ, and RV Stick. "The Treatment of Some Cyclic Thiocarbonates With Methyl Halide/Propylene Oxide." Australian Journal of Chemistry 40, no. 5 (1987): 795. http://dx.doi.org/10.1071/ch9870795.

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Treatment of thiocarbonates (OCSO) with methyl iodidelpropylene oxide at 80� can lead smoothly to the carbonate. In some cases, a competing process is the formation of iodo thiocarbonates ( OCOSMe ), and an explanation is provided for the product distributions observed. The corresponding reactions with methyl bromide and methyl chloride (as methyl chloroformate ) are much less efficient.

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4

Turhanen, Petri A., Janne Weisell, and Jouko J. Vepsäläinen. "Preparation of mixed trialkyl alkylcarbonate derivatives of etidronic acid via an unusual route." Beilstein Journal of Organic Chemistry 8 (November 20, 2012): 2019–24. http://dx.doi.org/10.3762/bjoc.8.228.

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A method to prepare four (3a–d) trialkyl alkylcarbonate esters of etidronate from P,P'-dimethyl etidronate and alkyl chloroformate was developed by utilizing unexpected demethylation and decarboxylation reactions. The reaction with the sterically more hindered isobutyl chloroformate at a lower temperature (90 °C) produced the P,P'-diester (2) as a stable intermediate product. A possible reaction mechanism is discussed to explain these methyl substitutions. These unusual reactions also clarify why it is difficult to prepare alkylcarbonate prodrugs from bisphosphonates. The compounds prepared we

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5

Wang, Bing-Tao, Hua-Dong Yue, Shu-Ping Luo, Li-Ping Wang, and Dan-Qian Xu. "Diphenyl-5,6,7,7a-tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (2007): o1108—o1109. http://dx.doi.org/10.1107/s1600536807004394.

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The title compound, C18H17NO2, synthesized from enantiomerically pure L-proline, methyl chloroformate and a Grignard reagent, crystallizes with two molecules in the asymmetric unit. A chair conformation is adopted by the two fused five-membered rings.

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6

Kevill, Dennis N., Jong Chul Kim, and Jin Burm Kyong. "Correlation of the Rates of Solvolysis of Methyl Chloroformate with Solvent Properties." Journal of Chemical Research 23, no. 2 (1999): 150–51. http://dx.doi.org/10.1177/174751989902300242.

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The specific rates of solvolyis of methyl chloroformate are very well correlated by the extended Grunwald–Winstein equation over a wide range of solvents; the pathway is believed to be predominantly addition–elimination, except that a positive deviation for solvolysis in 90% 1,1,1,3,3,3-hexafluoropropan-2-ol suggests an 80% contribution from an ionisation mechanism.

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7

Groner, P., C. L. Tolley, and J. R. Durig. "A microwave and ab initio structure determination of methyl chloroformate." Chemical Physics 142, no. 3 (1990): 381–94. http://dx.doi.org/10.1016/0301-0104(90)80033-t.

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8

Zeng, Xiao-Qing, Mao-Fa Ge, Lin Du, Zheng Sun, and Dian-Xun Wang. "Experimental and theoretical study of the electronic structure of methyl chloroformate and methyl cyanoformate." Journal of Molecular Structure 800, no. 1-3 (2006): 62–68. http://dx.doi.org/10.1016/j.molstruc.2006.03.080.

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9

Thavaneswaran, Shanti, Kristy McCamley, and Peter J. Scammells. "N-Demethylation of Alkaloids." Natural Product Communications 1, no. 10 (2006): 1934578X0600101. http://dx.doi.org/10.1177/1934578x0600101008.

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The removal of an N-methyl group, or N-demethylation, is a useful chemical transformation in organic synthesis which has particular importance in the field of alkaloid chemistry. Historically, tertiary N-methyl alkaloids have been N-demethylated using the same methods as for N-dealkylating tertiary amines. Such methodologies have included the von Braun reaction, the use of chloroformate and azodicarboxylate reagents and the Polonovski reaction, amongst others. Photochemical and biochemical procedures have also been successfully employed. This review will examine these N-demethylation procedure

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10

Chen, Francis M. F., and N. Leo Benoiton. "N,N-Dialkoxycarbonylamino acid formation from a mixed anhydride through intramolecular urethane acylation." Canadian Journal of Chemistry 65, no. 6 (1987): 1228–29. http://dx.doi.org/10.1139/v87-207.

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Methoxycarbonylation at the urethane nitrogen of N-benzyloxycarbonyl- and N-methoxycarbonylvaline has been identified as a side reaction accompanying the aminolysis of the mixed anhydride formed from the acid and methyl chloroformate when the anhydride is coupled in aqueous dimethylformamide and the nucleophile is an amino acid anion. The side reaction occurs to a lesser but still significant extent when the activated residue is leucyl.

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11

Byrne, Brian, and Louise M. Lafleur Lawter. "The preparation of trimethylsulfonium chloride from methyl chloroformate and dimethyl sulfide." Tetrahedron Letters 27, no. 11 (1986): 1233–36. http://dx.doi.org/10.1016/s0040-4039(00)84225-2.

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12

Arbain, D., J. Langley, K. Picker, and WC Taylor. "The Determination of Chirality of N-Methyl- and N,N-Dimethyl-phenylalanine by G.L.C." Australian Journal of Chemistry 44, no. 6 (1991): 887. http://dx.doi.org/10.1071/ch9910887.

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The chirality of N- methylphenylalanine enantiomers can be determined on a micro scale by g.l.c . of N-pentafluoropropionyl amino acid isopropyl esters on a Chirasil -L-Val capillary column. N,N- Dimethylphenylalanine enantiomers cannot be similarly derivatized and cannot be separated. However, prior treatment with ethyl chloroformate followed by acid hydrolysis effects demethylation to the N-methyl analogues which can then be derivatized for g.l.c . Contrary to literature reports N-methylphenylalanine can be prepared by reductive alkylation of phenylalanine.

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13

Kevill, Dennis N., Jong Chul Kim, and Jin Burm Kyong. "Correlation of the Rates of Solvolysis of Methyl Chloroformate with Solvent Properties." Journal of Chemical Research, no. 2 (1999): 150–51. http://dx.doi.org/10.1039/a808929i.

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14

Chen, Francis M. F., and N. Leo Benoiton. "The preparation and reactions of mixed anhydrides of N-alkoxycarbonylamino acids." Canadian Journal of Chemistry 65, no. 3 (1987): 619–25. http://dx.doi.org/10.1139/v87-106.

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Pure mixed anhydrides R1OCO-Xxx-O-COOR2 (Xxx=NHCHRCO) have been obtained by reaction of N-alkoxycarbonyl-amino acids R1OCO-Xxx-OH with alkyl chloroformate R2OCOCl (R2 = methyl, ethyl, isobutyl, menthyl) in the presence of N-methylmorpholine or N-methylpiperidine (NMP) in dichloromethane at −5 °C, followed by washing the mixtures with aqueous solutions and removal of the solvent. R1OCO-Xxx-O-COOR2 (R2 = ethyl, tert-butyl) have been obtained by reaction of R1OCO-Xxx-O−•+HNMP with the corresponding dialkyl dicarbonates followed by the same work-up. Mixed anhydride generation is much slower when t

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15

Best, WM, RW Dunlop, RV Stick та ST White. "All About 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucosyl Trichloroacetimidate". Australian Journal of Chemistry 47, № 3 (1994): 433. http://dx.doi.org/10.1071/ch9940433.

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Treatment of 1,3,4,6-tetra-O-acetyl-2-(o-carboxybenzoylamino )-2-deoxy-β-D-glucose with ethyl chloroformate , followed by workup and treatment with methanol, did not give 1,3,4,6-tetra O-acetyl-2-deoxy-2-phthalimido-β-D-glucose as reported in the literature, but rather the methyl ester 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(o- methoxycarbonylbenzoylamino )-β-D-glucose. The formation of this methyl ester is believed to proceed via 1,3,4,6-tetra-O-acetyl-2-deoxy-2- [(3′-oxo-1′,3′-dihydroisobenzofuran-1′-ylidene)amino]-β-D-glucose which was also formed from the amido carboxylic acid by treatment with

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16

Hulinská, Hana, Petr Taufmann, Hana Frycová, and Miroslav Protiva. "1-Methyl-, 1-phenyl-, and 1-(2-(2-dimethylaminoethoxy)-phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and their 2-substituted derivatives: Synthesis and pharmacological screening." Collection of Czechoslovak Chemical Communications 53, no. 2 (1988): 373–80. http://dx.doi.org/10.1135/cccc19880373.

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1-Methyl- and 1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (I and IV) were transformed via the chloroacetyl derivatives II and V to the 4-methylpiperazinoacetyl compounds III and VI; compound VI inhibits effectively the formation of the indomethacin-induced gastric ulcers in rats but is devoid of anticholinergic activity and does not inhibit the gastric secretion in rats. Reaction of tryptamine with 2-(2-dimethylaminoethoxy)benzaldehyde afforded compound IX which proved inactive in tests for antidepressant activity. Compounds IV and IX were treated with ethyl chloroformate and gave carba

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17

Lei, Kang, Dong-Wei Sun, Yuan-Yuan Tao, and Xiao-Hua Xu. "A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives." Australian Journal of Chemistry 69, no. 1 (2016): 98. http://dx.doi.org/10.1071/ch15267.

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A new protocol for total synthesis of natural product frutinone A was accomplished in three steps by using inexpensive 2′-hydroxyacetophenone as starting material. The key intermediate 3-(2-chlorobenzoyl)-4-hydroxycoumarin was synthesized in one pot through Baker–Venkataraman rearrangement of 2-acetylphenyl 2-chlorobenzoate followed by introduction of methyl chloroformate under basic conditions. Then, base-promoted intramolecular nucleophilic substitution reaction of 3-(2-chlorobenzoyl)-4-hydroxycoumarin provided frutinone A in excellent yield. The synthetic route features good yield, transiti

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18

Chen, Wen-Ping, Xiao-Yuan Yang, Adrian D. Hegeman, William M. Gray, and Jerry D. Cohen. "Microscale analysis of amino acids using gas chromatography–mass spectrometry after methyl chloroformate derivatization." Journal of Chromatography B 878, no. 24 (2010): 2199–208. http://dx.doi.org/10.1016/j.jchromb.2010.06.027.

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19

Cao, Jian, Juan Chu, and Ke-Da Zhang. "A new initiator cholesteryl chloroformate for cupper-based atom transfer radical polymerization of methyl methacrylate." Chinese Journal of Chemistry 22, no. 12 (2010): 1436–39. http://dx.doi.org/10.1002/cjoc.20040221212.

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20

Bell, M. J., K. C. Lau, M. J. Krisch, D. I. G. Bennett, L. J. Butler, and F. Weinhold. "Characterization of the Methoxy Carbonyl Radical Formed via Photolysis of Methyl Chloroformate at 193.3 nm." Journal of Physical Chemistry A 111, no. 10 (2007): 1762–70. http://dx.doi.org/10.1021/jp066056i.

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21

Fu, Irong, and Larry D. Bowers. "Micro-quantification of cyclosporine and its metabolites and determination of their spectral absorptivities." Clinical Chemistry 37, no. 7 (1991): 1185–90. http://dx.doi.org/10.1093/clinchem/37.7.1185.

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Abstract We report a micromethod for the analysis of cyclosporine (CsA), based on quantification of its constituent amino acids. The amino acids were released by gas-phase hydrolysis, derivatized with fluorenylmethyl chloroformate, and separated and analyzed in a reversed-phase HPLC system. The imprecision (CV) of the amino acid analysis was less than 4%, and several determinations of the amount of standard CsA were within 1% of the weighed material. The detection limits (signal-to-noise ratio = 2) were 500 fmol for ultraviolet detection and 100 fmol for fluorescence detection. We also used th

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22

Szilágyi, István, Sándor Dóbé, Tibor Bérces, Ferenc Márta, and Béla Viskolcz. "Direct Kinetic Study of Reactions of Hydroxyl Radicals with Alkyl Formates." Zeitschrift für Physikalische Chemie 218, no. 4 (2004): 479–92. http://dx.doi.org/10.1524/zpch.218.4.479.29198.

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AbstractRate coefficients were determined for the gas phase reactions of hydroxyl radicals with a series of alkyl formats. Experiments were carried out using the isothermal fast flow method coupled with resonance fluorescence detection. The obtained room temperature rate coefficients are (in 10−13cm3 molecule−1s−1 units): 1.83 ± 0.33 (methyl formate), 9.65 ± 0.43 (ethyl formate), 18.73 ± 0.83 (isopropyl formate), 6.77 ± 0.38 (tert-butyl formate) and 1.62 ± 0.13 (methyl chloroformate). These results are compared with the literature data. In addition estimations are made for the partial reactivi

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23

Still, Ian WJ, Rosanne Natividad-Preyra, and F. Dean Toste. "A versatile synthetic route to 1,5-dithiocins from o-mercapto aromatic aldehydes." Canadian Journal of Chemistry 77, no. 1 (1999): 113–21. http://dx.doi.org/10.1139/v98-230.

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An earlier procedure for the facile preparation of benzo-fused 1,5-dithiocins 2a-2c from o-mercapto- benzaldehydes has been improved and shown to be capable of extension to the preparation of several naphthalene-derived analogues. The general method also afforded several N-alkylated 1,5-dithiocins 4, 5 by replacing NH3 with the appropriate primary amine. It was found that N-acylation of the 1,5-dithiocins was successful only with methyl chloroformate. Attempted N-phenylation met with limited success but was shown to be unnecessary since even the less reactive aniline readily undergoes the gene

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24

Valenta, Vladimír, Marie Vlková, Martin Valchář, Karel Dobrovský, and Zdeněk Polívka. "Potential antidepressants: 3-Aryl-3-(arylthio)propylamines as selective inhibitors of 5-hydroxytryptamine re-uptake in the brain." Collection of Czechoslovak Chemical Communications 56, no. 7 (1991): 1525–33. http://dx.doi.org/10.1135/cccc19911525.

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4-(Trifluoromethyl)thiophenol, 2-methylthiophenol, 2-methoxythiophenol, and 1-naphthalenethiol were transformed by reactions with N,N-dimethyl-3-chloro-3-phenylpropylamine to N,N-dimethyl-3-aryl-3-(arylthio)propylamines IVa-VIIa. These afforded the secondary amines IVb-VIIb by treatment with ethyl chloroformate and by the following hydrolysis and decarboxylation of the primarily formed N-(methyl)-N-(ethoxycarbonyl) analogues. Reaction of 1-naphthalenethiol with the 4-toluenesulfonic ester X in situ gave the thiophene analogue VIIIa which was similarly demethylated to VIIIb. Some of the prepare

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25

Mahmoud, M. R., A. A. Shalaby, T. A. Gad, and A. A. El-Khamry. "A facile synthesis and heteroannulation of pyrido[2,3-d]pyrimidine and related heterocyclic systems." Journal of Chemical Research 2009, no. 10 (2009): 612–15. http://dx.doi.org/10.3184/030823409x12523324765777.

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7-Amino-1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-(3,4,5-trimethoxyphenyl)pyrido[2,3- d]pyrimidine (1) was prepared and reacted with methyl iodide and ethyl chloroacetate to give the S-alkylated products 2 and 3, respectively. The reaction of 1 or 3 with hydrazine hydrate yielded the same 2-hydrazino derivative 4. Treatment of 4 with 2,4-pentanedione, 2-acetylcyclohexanone and ethyl acetoacetate afforded the corresponding pyrazolylpyrido[2,3- d]pyrimidine derivatives (5–7), while phthalic anhydride gave the phthalazinyl compound 8. Ethoxymethylenemalononitrile with the hydrazine 4 formed the fused 1

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26

El Seoud, Omar A., and Keiko Takashima. "The Spontaneous Hydrolysis of Methyl Chloroformate: A Physical Chemistry Experiment for Teaching Techniques in Chemical Kinetics." Journal of Chemical Education 75, no. 12 (1998): 1625. http://dx.doi.org/10.1021/ed075p1625.

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27

Liebich, H. M., E. Gesele, H. G. Wahl, C. Wirth, J. Wöll, and P. Hušek. "Identification of side-products formed by derivatization of 2-hydroxycarboxylic acids with methyl and ethyl chloroformate." Journal of Chromatography A 626, no. 2 (1992): 289–93. http://dx.doi.org/10.1016/0021-9673(92)85423-q.

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28

Kartal, Aslıhan Arslan, Umit Divrikli, and Latif Elci. "Determination of Chlorophenols in Wastewater with Methyl Chloroformate Derivatization, Solid Phase Extraction, and Gas Chromatography–Mass Spectrometry." Analytical Letters 48, no. 17 (2015): 2723–38. http://dx.doi.org/10.1080/00032719.2015.1046551.

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29

Lu, Ling, Jim-Min Fang, Gene-Hsiang Lee, and Yu Wang. "One-Pot Formation of Carbonates from the Reactions of Carbonyl Compounds with Samarium Diiodide and Methyl Chloroformate." Journal of the Chinese Chemical Society 44, no. 3 (1997): 279–89. http://dx.doi.org/10.1002/jccs.199700043.

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30

Villas-Bôas, Silas Granato, Daniel Gutierrez Delicado, Mats Åkesson, and Jens Nielsen. "Simultaneous analysis of amino and nonamino organic acids as methyl chloroformate derivatives using gas chromatography–mass spectrometry." Analytical Biochemistry 322, no. 1 (2003): 134–38. http://dx.doi.org/10.1016/j.ab.2003.07.018.

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31

Zampolli, M. G., G. Basaglia, F. Dondi, R. Sternberg, C. Szopa, and M. C. Pietrogrande. "Gas chromatography–mass spectrometry analysis of amino acid enantiomers as methyl chloroformate derivatives: Application to space analysis." Journal of Chromatography A 1150, no. 1-2 (2007): 162–72. http://dx.doi.org/10.1016/j.chroma.2006.12.033.

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32

Brown, RFC, KJ Coulston, FW Eastwood, and MP Hill. "Synthesis of Precursors Suitable for Pyrolytic Fragmentation to Pentatetraenone." Australian Journal of Chemistry 41, no. 2 (1988): 215. http://dx.doi.org/10.1071/ch9880215.

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Reaction of 2-phenylselenopropanoyl chloride with methyl ( triphenylphosphoranylidene ) ethanoate yielded methyl 4- phenylselenopenta-2,3-dienoate (3). Distillation of the ester (3) gave dimethyl (E,E)-3′,4′-dimethylcyclobut-3′-ene-1′,2′- diylidenebisethanoate (5) and oxidation of (3) with potassium peroxymonosulfate yielded methyl 2-oxopent-3-ynoate (8). The ester (3) with cyclopentadiene at 160-180° gave a Diels-Alder adduct methyl 3- (1′-phenylselenoethylidene) bicyclo [2.2.1]hept-5-ene-2-carboxylate (4) as a mixture of four isomers. Treatment of the mixture with lithium diisopropylamide an

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33

Mochizukiy, Amane, Michie Sakamotoy, Masahiro Yoshiokay, Yuji Hottay, Takahiro Fukuokay, and Mitsuru Ueda. "Synthesis and Properties of a Novel Thermostable Polymer: Fluorinated Polycarbodiimide." High Performance Polymers 9, no. 4 (1997): 385–95. http://dx.doi.org/10.1088/0954-0083/9/4/003.

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A new fluorinated linear polycarbodiimide (F-PCD) was synthesized by solution polycondensation of a new fluorinated diisocyanate monomer, 4″, 4″′-(hexafluoroisopropylidene) bis(4-phenoxyphenyl isocyanate) (HPI) in the presence of 3-methyl-1-phenyl-2-phospholene-1-oxide (PMO). HPI was prepared from 4″, 4″′-(hexafluoroisopropylidene)bis(4-phenoxyaniline) (HPA) by three steps. The reaction of HPA with phenyl chloroformate gave the corresponding carbamate, which upon reaction with trimethylsilylchloride (TMS-Cl)-triethylamine (TEA), followed by thermal decomposition, provided HPI. The polymer havi

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34

Bremner, JB, and W. Jaturonrusmee. "Synthesis of Some Naphthothiadiazolophanes. Derivatives of 4,10,14-Ethenylylidene-7H-[1,2,3]thiadiazolo[5,4-e]azacyclotridecine and 4,11,15-Ethenylylidene[1,2,3]thiadiazolo[5,4-f]azacyclotetradecine." Australian Journal of Chemistry 42, no. 11 (1989): 1951. http://dx.doi.org/10.1071/ch9891951.

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Reaction of 7,8-dimethoxy-1,2,4,5,1lb, 11c-hexahydrobenzo [de]pyrrolo[3,2,1-ij][1,2,3]thiadiazolo[4,5-g]quinoline (3a) and 8,9-dimethoxy-2,3,5,6,12b,12c-hexahydro-1H-[1,2,3]thiadiazolo-[5',4':3,4]naphtho[2,1,8-ijalquinoline (3b) with cyanogen bromide in the presence of potassium carbonate gave the naphthothiadiazolophanes 12,13-dimethoxy-5,6,8,9-tetrahydro-4,10,14- ethenylylidene-7H-[1,2,3]thiadiazolo[5,4-e]azacyclotridecine-7-carbonitrile (4a) and 13,14-di-methoxy-6,7,9,10-tetrahydro-4,11,15-ethenylylidene[1,2,3]thiadiazolo[5,4-f]azacyclotetradecine-8(5H)-carbonltrile (4b) in 39 and 89% yield

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35

Polívka, Zdeněk, Vladimír Valenta, Karel Šindelář, et al. "Potential antidepressants: Saturated side chain amines derived from 6,11-dihydrodibenzo[b,e]thiepin and 4,9-dihydrothieno[2,3-c]-2-benzothiepin." Collection of Czechoslovak Chemical Communications 54, no. 1 (1989): 235–47. http://dx.doi.org/10.1135/cccc19890235.

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Reduction of IV with hydroiodic acid afforded almost quantitatively the spirocyclic amino sulfide VII, evidently via V and VI. The carbamate II was chlorinated with N-chlorosuccinimide, the product (XII) was reacted with phenylmagnesium bromide and then reduced with LiAlH4 to give the 6-phenyl derivative X of the antidepressant agent hydrothiadene (I). Treatment of 11-methyl-6,11-dihydrodibenzo[b,e]thiepin (XIII) with butyllithium followed by alkylation with 3-dimethylaminopropyl chloride resulted in 6-(3-dimethylaminopropyl) derivative XIV. Reaction of XIV with ethyl chloroformate and the fol

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36

Smart, Kathleen F., Raphael B. M. Aggio, Jeremy R. Van Houtte, and Silas G. Villas-Bôas. "Analytical platform for metabolome analysis of microbial cells using methyl chloroformate derivatization followed by gas chromatography–mass spectrometry." Nature Protocols 5, no. 10 (2010): 1709–29. http://dx.doi.org/10.1038/nprot.2010.108.

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37

Rawlinson, Catherine, Lars G. Kamphuis, Joel P. A. Gummer, Karam B. Singh, and Robert D. Trengove. "A rapid method for profiling of volatile and semi-volatile phytohormones using methyl chloroformate derivatisation and GC–MS." Metabolomics 11, no. 6 (2015): 1922–33. http://dx.doi.org/10.1007/s11306-015-0837-0.

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38

Sturdivant, Jill, and Mitchell deLong. "Asymmetric Synthesis of Netarsudil: A New Therapeutic for Open-Angle Glaucoma." Synthesis 51, no. 04 (2018): 953–59. http://dx.doi.org/10.1055/s-0037-1610310.

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The asymmetric synthesis of a Rho kinase/norepinephrine transport inhibitor, netarsudil, the active component in the recently FDA-approved product Rhopressa™, is described herein. This concise six-step synthetic route utilizes the 2,4-dimethylbenzoate ester of a phenylacetic acid as the backbone of the β-amino acid’s framework. A chiral enolate of the Evans auxiliary, (R)-4-benzyloxazolidin-2-one, is used to direct the formation of the (S)-stereocenter by incorporating the N-Boc-protected β-amino methyl arm with high diastereoselectivity (96:4 dr) using N-Boc-1-aminomethylbenzotriazole as the

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39

Zhao, Jiayi, Rong Chai, Yiping Han, Jing Sheng, Chong Bai, and Haidong Huang. "Case report of the successful treatment of lung injury caused by occupational exposure to methyl chloroformate and literature review." Medicine 97, no. 17 (2018): e0288. http://dx.doi.org/10.1097/md.0000000000010288.

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FORSYTHE, KELSEY M., DANIEL H. ROBERTSON, and QI-HUANG ZHENG. "AB INITIO MO CALCULATION STUDIES FOR SEVERAL NOVEL ENTRIES TO TROPANE COMPOUNDS." Journal of Theoretical and Computational Chemistry 03, no. 03 (2004): 305–23. http://dx.doi.org/10.1142/s0219633604001069.

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Tropane alkaloids are generally known as anticholinergics. Radiolabeled tropane compounds could be brain imaging agents used in biomedical imaging technique positron emission tomography (PET). A novel entry to aryltropane analogs of cocaine was developed based on the conjugate addition reaction of Grignard reagents phenylmagnesium (10), (4'-isopropenylphenyl)magnesium (11), or 2-naphthylmagnesium bromide (12) to α,β-unsaturated esters anhydroecgonine methyl ester (9) or t-butyl ester (13) which gave several aryltropanes (1–8) with high binding affinities for dopamine and serotonin transporters

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41

Majewski, Marek, and Guo-Zhu Zheng. "Stereoselective deprotonation of tropinone and reactions of tropinone lithium enolate." Canadian Journal of Chemistry 70, no. 10 (1992): 2618–26. http://dx.doi.org/10.1139/v92-330.

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Tropinone (6) was deprotonated with lithium diisopropylamide and with chiral lithium amides (18–24) and the resulting enolates (two enantiomers) were treated with electrophiles. The aldol reaction with benzaldehyde and deuteration were both diastereoselective. The former yielded only one isomer (exo, anti) of the aldol 8a; the latter proceeded from the exo face. This selectivity permitted us to probe the deprotonation of tropinone with lithium amides; it was concluded that the reaction involves predominantly the exo axial protons. The reaction of tropinone enolate with ethyl chloroformate led,

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Vancompernolle, Bram, Kim Croes, and Geert Angenon. "Optimization of a gas chromatography–mass spectrometry method with methyl chloroformate derivatization for quantification of amino acids in plant tissue." Journal of Chromatography B 1017-1018 (April 2016): 241–49. http://dx.doi.org/10.1016/j.jchromb.2016.02.020.

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Schottenberger, Herwig, Michael Buchmeiser, Johann Polin, and Karl-Eberhard Schwarzhans. "Ferrocen-Derivate der Quadrat- und Propiolsäure. Synthesen und Reaktionen / Ferrocene Derivatives of Squaric Acid and Propiolic Acid. Syntheses and Reactions." Zeitschrift für Naturforschung B 48, no. 11 (1993): 1524–32. http://dx.doi.org/10.1515/znb-1993-1110.

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Concepts for linking ferrocene derivatives with conjugated squarate and propiolate based spacer systems have been investigated. Coupling of 3,4-dichlorocyclobut-3-ene-1,2-dione (squaric acid dichloride) with cuproferrocene • dimethylsulfide resulted in 3-chloro-4-ferrocenylcyclobut-3-ene-1,2-dione (ferrocenylsemisquaric acid chloride) and 3,4-diferrocenylcyclobut-3-ene-1,2-dione. Ferrocenylsemisquaric acid chloride was further treated with ethynylferrocene and 4-ethynyl-4-(ferrocenylethynyl)tolan, respectively, to form the corresponding mixed squaric diketones, which required Zn/Pd mediated co

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MANADA, Noriaki, Masato MURAKAMI, Yasushi YAMAMOTO, and Toshio KURAFUJI. "Preparation of Dimethyl Carbonate in the Gas-phase Reaction. Release of Cl-compound from PdCl2 Catalyst and Effect of Methyl Chloroformate." NIPPON KAGAKU KAISHI, no. 11 (1994): 985–91. http://dx.doi.org/10.1246/nikkashi.1994.985.

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Nattouf, H., C. Davrinche, M. Sinet, and R. Farinotti. "High-performance liquid chromatographic assay for 3′-amino-3′-deoxythymidine in plasma, with 9-fluorenyl methyl chloroformate as the derivatization agent." Journal of Chromatography B: Biomedical Sciences and Applications 664, no. 2 (1995): 365–71. http://dx.doi.org/10.1016/0378-4347(94)00499-u.

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Madsen, René Bjerregaard, Mads Mørk Jensen, Anders Juul Mørup, et al. "Using design of experiments to optimize derivatization with methyl chloroformate for quantitative analysis of the aqueous phase from hydrothermal liquefaction of biomass." Analytical and Bioanalytical Chemistry 408, no. 8 (2016): 2171–83. http://dx.doi.org/10.1007/s00216-016-9321-6.

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Rádl, Stanislav, Petr Hezký, Petr Konvička, and Ivan Krejčí. "Synthesis and Analgesic Activity of Some Substituted 1-Benzofurans and 1-Benzothiophenes." Collection of Czechoslovak Chemical Communications 65, no. 7 (2000): 1093–108. http://dx.doi.org/10.1135/cccc20001093.

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2-Benzoyl- and 2-(pyridylcarbonyl)-1-benzofuran-3-amines were prepared from 2-hydroxybenzonitrile and corresponding bromoethanone derivatives. 2-Benzoyl- and 2-(pyridylcarbonyl)-1-benzothiophene-3-amines were prepared analogously from 2-sulfanylbenzonitrile. 2-Benzoyl-1-benzofuran-3-amine treated with acetic anhydride or ethyl chloroformate provided the corresponding N-acetyl or N-ethoxycarbonyl derivatives. These N-activated compounds were alkylated with ethyl bromoacetate to provide ethyl N-acetyl-N-(2-benzoyl-1-benzofuran-3-yl)glycinate and ethyl N-(2-benzoyl-1-benzofuran-3-yl)-N-ethoxycarb

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Logvinenko, Ivan G., Violetta G. Dolovanyuk та Ivan S. Kondratov. "The preparative synthetic approach to 4-(triﬂuoromethoxy)piperidine and 4-(triﬂuoromethoxymethyl)piperidine". Journal of Organic and Pharmaceutical Chemistry 19, № 1(73) (2021): 3–9. http://dx.doi.org/10.24959/ophcj.21.222669.

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Aim. To develop a convenient synthetic approach for the preparation of multigram amounts of 4-(triﬂuoromethoxy)-piperidine and 4-(triﬂuoromethoxymethyl)piperidine – promising building blocks for medicinal chemistry.Results and discussion. 4-(Triﬂuoromethoxy)piperidine (8.4 g) and 4-(triﬂuoromethoxymethyl)piperidine (12.9 g) were synthesized in 5 stages starting from 4-hydroxypiperidine (the overall yield 40 %) and 4-(hydroxymethyl)piperidine (the overall yield 13.5 %), respectively.Experimental part. The first stage of the synthetic strategy was acylation of 4-hydroxypiperidine with benzoyl ch

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Wachsmuth, Christian J., Katja Dettmer, Sven A. Lang, Maria E. Mycielska, and Peter J. Oefner. "Continuous Water Infusion Enhances Atmospheric Pressure Chemical Ionization of Methyl Chloroformate Derivatives in Gas Chromatography Coupled to Time-of-Flight Mass Spectrometry-Based Metabolomics." Analytical Chemistry 86, no. 18 (2014): 9186–95. http://dx.doi.org/10.1021/ac502133r.

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Rubino, Federico M., Marco Pitton, Daniela Di Fabio, et al. "Measurement of S-methylcysteine and S-methyl-mercapturic acid in human urine by alkyl-chloroformate extractive derivatization and isotope-dilution gas chromatography-mass spectrometry." Biomedical Chromatography 25, no. 3 (2011): 330–43. http://dx.doi.org/10.1002/bmc.1451.

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