Process for preparing (R) and (S)-1,2-isopropylideneglycerol by crystallizing racemic benzoyl ester

US5332674A · kind A · utility

Assignee

• Ministero dell 'Universita'e della Ricerca Scientifica e Technologica · IT

Inventors

• Daniele Bianchi · Milano, IT
• Aldo Bosetti · Vercelli, IT
• Pietro Cesti · Trecate, IT
• Paolo Golini · Reggio nell'Emilia, IT
• Carlo Pina · Milano, IT

Key dates

• Filing date: Feb 12, 1993
• Grant date: Jul 26, 1994
• Expiry date: Feb 12, 2013

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C12P41/004
• WIPO field: Biotechnology
• WIPO sector: Chemistry

Abstract

A process is described for separating the optical isomers of 1,2-isopropylideneglycerol, of formula (I), comprising partially stereoselective enzymatic hydrolysis of 1,2-isopropylideneglycerol benzoyl ester (II) catalyzed by a free or immobilized lipase, the hydrolysis being conducted in the presence of a cosolvent and followed by crystallization enabling crystals of (II) in raceme form and mother liquor containing (II) in the form of the pure enantiomer to be selectively obtained. The compound (I) is widely used industrially as an intermediate in the synthesis of chiral drugs such as (R)-(-)-carnitine, (S)-beta-blockers, (S)-antiviral agents, analgesic drugs etc.