Process for preparing optically active allophenylnorstatin deriv

Details Process for preparing optically active allophenylnorstatin deriv Process for preparing optically active allophenylnorstatin deriv

1996-03-01

1996-12-03

Shaver, Paul F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

556419, 560 23, 562444, C07F 708, C07F 710

Patent

active

055810071

ABSTRACT:
A process for preparing an optically active (2S,3S)-allophenylnorstatin derivative (I) is disclosed, comprising asymmetrically hydrogenating a 4-phenyl-2-halogeno-3-oxobutyric ester (III) in the presence of a ruthenium-phosphine complex to obtain a 4-phenyl-(2S)-halogeno-(3R)-hydroxybutyric ester (IV), epoxidizing the ester (IV) in the presence of a base to obtain a 4-phenyl-(2S,3R)-epoxybutyric ester (V), reacting the ester (V) with a tri(lower alkyl)silylazide or a (lower alkyl)diarylsilylazide in the presence of a Lewis to obtain a (3S)-azido-4-phenyl-(2S)-trisubstituted silyloxybutyric ester (VI), hydrogenolyzing the ester (VI) into a (2S,3S)-allophenylnorstatin derivative (VII), protecting the amino group of the compound (VII), and, if desired, hydrolyzing the compound before or after the amino group protection. Compounds (I) can be obtained at high optical purity safely and in good yield.

REFERENCES:
patent: 5516926 (1996-05-01), Kim et al.
patent: 5516927 (1996-05-01), Kim et al.

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