Joseph P Duran

US Patent:

58409610, Nov 24, 1998

Filed:

Jul 10, 1997

Appl. No.:

8/890907

Inventors:

James Richard Behling - Lindenhurst IL
Mark Laurence Boys - Mt. Prospect IL
Pierre-Jean Colson - Skokie IL
Wendel William Doubleday - Encinitas CA
Joseph Edward Duran - Chicago IL
Payman N. Farid - Vernon Hills IL
Carl Matthew Knable - Mt. Prospect IL
Frank Walter Muellner - Hinsdale IL
Sean Thomas Nugent - Grayslake IL
Ravindra S. Topgi - Palatine IL

Assignee:

G. D. Searle & Co. - Chicago IL

International Classification:

C07C22900

US Classification:

560172

Abstract:

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.