Process for the synthesis of azetidinones

US6207822A · kind A · utility

Assignee

• SCHERING CORPORATION · US

Inventors

• Tiruvettipuram K. Thiruvengadam · Kendall Park, US
• Xiaoyong Fu · Edison, US
• Chou-Hong Tann · Berkeley Heights, US
• Timothy L. McAllister · Westfield, US
• John S. Chiu · Parsippany, US
• Cesar Colon · Rahway, US

Key dates

• Filing date: Dec 5, 1999
• Grant date: Mar 27, 2001
• Expiry date: Dec 5, 2019

Classification

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

Abstract

This invention provides a process for preparing the hypocholesterolemic compound ##STR1## comprising: PA1 (a) reacting p-fluorobenzoylbutyric acid with pivaloyl chloride and acylating the product with a chiral auxiliary to obtain a ketone of formula IV: ##STR2## PA1 (b) reducing the ketone of formula IV in the presence of a chiral catalyst to an alcohol: PA1 (c) reacting the chiral alcohol of step (b), an imine and a silyl protecting agent, then condensing the protected compounds to obtain a .beta.-(substituted-amino)amide of formula VII: ##STR3## PA1 (d) cyclizing the .beta.-(substituted-amino)amide of formula VII with a silylating agent and a fluoride ion catalyst to obtain a protected lactam of the formula VIII: ##STR4## and removing the protecting groups. The intermediates of formulas VII and VIII are also claimed.