New synthetic technology for efficient construction of alpha-hydroxy-beta-amino amides via the Passerini reaction |
| |
Authors: | Semple J E Owens T D Nguyen K Levy O E |
| |
Affiliation: | Department of Medicinal Chemistry, Corvas International, Inc., 3030 Science Park Road, San Diego, California 92121, USA. ed_semple@corvas.com |
| |
Abstract: | [reaction: see text] The Passerini reaction of N-protected amino aldehydes, isonitriles, and TFA using pyridine-type bases proceeds under mild conditions and directly affords alpha-hydroxy-beta-amino amide derivatives in moderate to high yields. These adducts are readily hydrolyzed to alpha-hydroxy-beta-amino carboxylic acids. Application of these key intermediates to concise syntheses of P(1)-alpha-ketoamide protease inhibitors is illustrated. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|