PROCESSES AND INTERMEDIATES FOR PREPARING A MACROCYCLIC PROTEASE INHIBITOR OF HCV

A process for preparing [(1 R ,2 R )-4-oxo-1,2-cyclopentanedicarboxylic acid II, by the resolution of racemic 4-oxo-1,2-cyclopentanedicarboxylic acid (V), said process comprising: (a) reacting 4-oxo-1,2-cyclopentanedicarboxylic acid (V) with brucine or ( 1R,2S )-(-)-ephedrine, thus preparing the bis...

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Bibliographic Details
Main Authors ORMEROD, Dominic John, DEPRÉ, Dominique Paul Michel, HORVATH, Andras
Format Patent
LanguageEnglish
French
German
Published 01.11.2017
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
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Summary:A process for preparing [(1 R ,2 R )-4-oxo-1,2-cyclopentanedicarboxylic acid II, by the resolution of racemic 4-oxo-1,2-cyclopentanedicarboxylic acid (V), said process comprising: (a) reacting 4-oxo-1,2-cyclopentanedicarboxylic acid (V) with brucine or ( 1R,2S )-(-)-ephedrine, thus preparing the bis-brucine or bis-( 1R , 2S )-(-)-ephedrine salt of (V), and (b) precipitating selectively the bis-brucine or bis-( 1R,2S )-( - )-ephedrine salt of (1 R ,2 R )-4-oxo-1,2-cyclopentanedicarboxylic acid II, while the bis-brucine or bis-( 1R,2S ) - (-)-ephedrine salt of [(1 S ,2 S )-4-oxo-1,2-cyclopentanedicarboxylic acid stays in solution; (c) liberating the acid II by removal of brucine or ( 1R , 2S )-(-)-ephedrine from the precipitated salt obtained in step (b).
Bibliography:Application Number: EP20170166514