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.
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Tagline:
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