Process for preparation of oxyglutaric acid ester derivatives

Details Process for preparation of oxyglutaric acid ester derivatives Process for preparation of oxyglutaric acid ester derivatives

1995-10-04

1998-02-10

Shaver, Paul F.

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

Organic compounds

Silicon containing

556404, 558 87, 560174, C07F 708

Patent

active

057171246

ABSTRACT:
A process for preparing an oxyglutaric acid ester derivative of the formula: ##STR1## in which each of R.sup.1 and R.sup.2 is C.sub.1-5 alkoxy, C.sub.1-7 aralkyloxy, C.sub.7-9 halogenated aralkyloxy or phenyl, R.sup.4 is a hydroxyl-protecting group, and R.sup.5 is C.sub.1-10 alkyl which may have a substituent, comprises the steps of reacting a methyl phosphonate derivative or methyl phosphine oxide derivative with an oxyglutaric acid mono-ester to give a reaction product which comprises an oxyglutaric acid derivative having a phosphorus-containing group and a pentenedioic acid mono-ester (by-product), removing the pendenedioic acid mono-ester from the reaction product to isolate the oxyglutaric acid derivative, and converting the isolated oxyglutaric acid derivative into the oxyglutaric acid ester derivative. A process for obtaining an optically active oxyglutaric acid ester derivative is also disclosed.

REFERENCES:
patent: 4686298 (1987-08-01), Karanewsky et al.
patent: 4804770 (1989-02-01), Karanewsky
patent: 5177239 (1993-01-01), Singh et al.
Heathcock et al., J. Chem. Med., 1987, Total Synthesis and Biological Evaluation of Structural Analogues of Compactin and Dihydromevinolin, pp. 1858-1873.

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