Selective precipitation of .alpha.-aryl carboxylic acid salts

US5380867A · kind A · utility

Assignee

• Hoechst Celanese Corporation · US

Inventors

• Apurba Bhattacharya · Port Aransas, US
• John R. Fritch · Port Aransas, US
• Carl D. Murphy · Port Aransas, US
• Larry D. Zeagler · Port Aransas, US
• Carina Araullo McAdams · Wilmington, US

Key dates

• Filing date: Oct 19, 1993
• Grant date: Jan 10, 1995
• Expiry date: Oct 19, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C51/487
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process is provided whereby S(+)-ibuprofen or R(-)-ibuprofen L-lysinate salt is produced by selective precipitation from a mixture containing enantiomers of ibuprofen and L-lysine. The quantity of L-lysine is not more than about a molar equivalent of the quantity of one of the enantiomers in the ibuprofen enantiomeric mixture. Upon precipitation of one ibuprofen enantiomer from the mixture, the overall precipitate and reaction mixture can be held for a sufficient period of time at a second temperature to allow the first precipitate to redissolve into the reaction mixture and the other ibuprofen enantiomer to precipitate out of the mixture in the salt form. Optically active ibuprofen is racemized by being heated at 100.degree. C. to 300.degree. C. in the substantial absence of other materials.