Asymmetric synthesis of chiral beta-amiNo acids
US5840961A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jul 10, 1997 |
| Grant date | Nov 24, 1998 |
| Priority date | — |
| Expiry date | Jul 10, 2017 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/582
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.