Stereoselective reduction of substituted oxo-butanes

C - Chemistry – Metallurgy – 12 – P

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C12P 7/02 (2006.01) C12P 13/00 (2006.01)

Patent

CA 2417086

The present invention relates to a process for the stereoselective enzymatic reduction of 1-halo-2-oxo-3-(protected)amino-4-substituted-butanes utilizing certain species of Rhodococcus and Brevibacterium. The product 1-halo-2-oxo-3- (protected)amino-4-substituted-butanes, which are useful as intermediates in the synthesis of compounds that are inhibitors of ACE, renin and HIV proteases, are obtained in high yield and, particularly, in very high diastereometric purity. The process is advantageously highly selective for the 1S,2S enantiomer of the product.

La présente invention concerne un procédé de réduction enzymatique stéréosélective de 1-halo-2-oxo-3-amino(protégé)-butanes substitués en position 4 utilisant certaines espèces de Rhodococcus et de Brevibacterium. Les 1-halo-2-hydroxy-3-amino(protégé)-butanes substitués en position 4, qui sont utilisés comme intermédiaires dans la synthèse des composés inhibiteurs de l'ACE, de la rénine et des protéases VIH, sont obtenus à haut rendement et présentent, en particulier, une grande pureté diastéréomérique. Ce procédé est particulièrement sélectif pour l'énantiomère 1S,2S du produit.

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