Preparation of [4S-(4.alpha.,7.alpha.,10a.beta.)]-4-amino-octahydro-5-oxo-7H-pyrido[2,1 -b] [1,3]thiazepine-7-carboxylic acid, methyl ester and salts thereof via novel disulfides

US6162913A · kind A · utility

Assignee

• Bristol-Myers Squibb Company · US

Inventors

• Jerome L. Moniot · Richboro, US
• Sushil K. Srivastava
• William J. Winter · Lebanon, US
• John J. Venit · New Brunswick, US
• Shankar Swaminathan · Braunschweig, DE
• Keith Ramig · Orange, US
• Paul Jass · Charles City, US
• Mark D. Schwinden · Holland, US
• John L. Dillon, Jr. · El Paso, US
• Saibaba Racha · Smithtown, US
• James H. Simpson · Fryeburg, US
• Chien-Kuang Chen · Taipei, TW
• Shawn K. Pack · Plainsboro, US

Key dates

• Filing date: Jul 8, 1999
• Grant date: Dec 19, 2000
• Expiry date: Jul 8, 2019

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

N-protected-L-homocysteine disulfide of the formula ##STR1## or an activated form thereof is reacted with (S)-2-amino-6,6-dimethoxyhexanoic acid, methyl ester to give the disulfide intermediate of the formula ##STR2## Cleavage of the disulfide bond followed by acid catalyzed cyclization produces the N-protected lactam of formula III which is useful for preparing the pharmaceutically active compound omapatrilat.