15028-40-7

Phenylglycine Methyl Ester Hydrochloride, is a substituted Glycine derivative, used as an intermediate for the synthesis of various pharmaceutical compounds. It is also a compound involved in the enzymic synthesis of D-(-)-α-Aminobenzyl penicillin by Penicillin Acylase.

General procedure for the synthesis of methyl 2-amino-2-phenylacetate hydrochloride from methanol and 2-amino-2-phenylacetic acid: a solution was prepared by dissolving 151 g (1 mole) of 2-amino-2-phenylacetic acid in 1.5 liters of methanol. To this solution, 2 molar equivalents (146 mmol) of thionyl chloride were slowly added at 0°C while maintaining stirring. The reaction mixture was stirred at 50°C for 6 hours. Upon completion of the reaction, the solvent was removed by vacuum evaporation to afford methyl 2-amino-2-phenylacetate hydrochloride in quantitative yield.

[1] Patent: US9464079, 2016, B2. Location in patent: Page/Page column 31; 32
[2] Russian Journal of General Chemistry, 2007, vol. 77, # 4, p. 581 - 585
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1942 - 1944
[4] The Journal of organic chemistry, 2002, vol. 67, # 11, p. 3687 - 3692
[5] Bulletin de la Societe Chimique de France, 1982, vol. 2, # 1-2, p. 75 - 83