Process for the synthesis of carbapenem intermidiates, and compounds produced

US6395894B2 · kind B2 · utility

Inventors

• Philip Pye · Guttenberg, US
• Paul J. Reider · Westfield, US
• Kai Rossen · Hanau, DE
• Ralph P. Volante · Rahway, US

Key dates

• Filing date: Apr 15, 1999
• Grant date: May 28, 2002
• Expiry date: Apr 15, 2019

Classification

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

Abstract

A process of synthesizing a compound of structural formula 6 is disclosed wherein R1 represents H or a suitable protecting group for an alcohol; R2 represents a benzyl, C1-6 alkyl or aryl; Y represents C1-3 alkyl, O, NH or S; X represents O, NH, or S and R5 represents a carboxy protecting group, comprising reacting a compound of formula 5: wherein R1, R2, R5, X and Y are as previously described with a phosphite or phosphonite reagent to produce a compound of formula 6. Further disclosed is an efficient method for the synthesis of a compound of formula 2: which comprises reacting a 4-acyl-2-azetidinone with a titanium, zirconium or hafnium enolate of a 1-hydroxy-2-butanone derivative.