Processes and Intermediates for Preparing a Macrocyclic Protease Inhibitor of HCV

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...

Ausführliche Beschreibung

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Bibliographische Detailangaben
Hauptverfasser: Ormerod Dominic John, Depre Dominique Paul Michel, Horvath Andras
Format: Patent
Sprache:eng
Schlagworte:
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Beschreibung
Zusammenfassung: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).