发明名称 |
Asymmetric synthesis of chiral beta-amiNo acids |
摘要 |
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 BrZnCH2CO2t-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.
|
申请公布号 |
US5840961(A) |
申请公布日期 |
1998.11.24 |
申请号 |
US19970890907 |
申请日期 |
1997.07.10 |
申请人 |
G. D. SEARLE & CO. |
发明人 |
BEHLING, JAMES RICHARD;BOYS, MARK LAURENCE;CAIN-JANICKI, KIMBERLY JO;COLSON, PIERRE-JEAN;DOUBLEDAY, WENDEL WILLIAM;DURAN, JOSEPH EDWARD;FARID, PAYMAN N.;KNABLE, CARL MATTHEW;MUELLNER, FRANK WALTER;NUGENT, SEAN THOMAS;TOPGI, RAVINDRA S. |
分类号 |
C07C227/18;C07C227/32;C07C229/08;C07C229/30;C07C229/34;C07D213/55;C07D213/61;C07D307/54;(IPC1-7):C07C229/00 |
主分类号 |
C07C227/18 |
代理机构 |
|
代理人 |
|
主权项 |
|
地址 |
|