Monsanto Company

G.d. Searle & Company

Ravindra S Topgi

John S Ng

Pierre-Jean Colson

Ping T Wang

Edward E Yonan

James R Behling

Sean T Nugent

Bryan H Landis

Payman N Farid

Carl M Knable

Kimberly J Cain-Janicki

Wendel W Doubleday

Mark L Boys

Carl Matthew Knable

Joseph Edward Duran

Frank Walter Muellner

Kimberly Jo Cain-Janicki

Mark Laurence Boys

Wendel William Doubleday

Joseph E Duran

Frank W Muellner

A method for preparing a chiral beta amino acid or its corresponding esters which comprises contacting a racemic beta amino acid, an acyl donor and Penicillin G acylase enzyme under conditions appropriate to stereoselectively acylate one enantiomer of the racemic beta amino acid to its corresponding N-acylated derivative whereby the opposite enantiomer of the beta amino acid is retained in enantiomerically enriched form.

Method and apparatus for preparation of chiral beta amino acids using penicilln G acylase

The invention herein is directed to a process for the preparation of ethyl 3S-amino-4-pentynoate which involves treating 3-(trimethylsilyl)-2-propynal with L-phenylglycinol in toluene to produce .alpha.S-��3-(trimethylsilyl)-2-propynylidene amino!benzenethanol; reacting .alpha.S-��3-(trimethylsilyl)-2-propynylidene!amino!benzenethanol with BrZnCH.sub.2 CO.sub.2 t-Bu in THF/NMP to produce 1,1-dimethylethyl 3S-�(2-hydroxy-1S-phenylethyl)amino!-5-(trimethylsilyl)-4-pentynoate; reacting the 1,1-dimethylethyl 3S-�(2-hydroxy-1S-phenylethyl)amino!-5-(trimethylsilyl)-4-pentynoate with sodium periodate to form 1,1-dimethylethyl 3S-�(phenylmethylene)amino!-5-(trimethylsilyl)-4-pentynoate; hydrolyzing 1,1-dimethylethyl 3S-�(phenylmethylene)amino!-5-(trimethylsilyl)-4-pentynoate to produce 1,1-dimethylethyl 3S-amino-5-(trimethylsilyl)-4-pentynoate; transesterifying 1,1-dimethyl 3S-amino-5-(trimethylsilyl)-4-pentynoate and desilylating to produce ethyl 3S-amino-4-pentynoate.

Asymmetric synthesis of chiral beta-amiNo acids

Growing community of inventors

Palatine, IL, United States of America

Ravindra S Topgi