Stereoselective preparation of 2-substituted succinic acid deriv

Details Stereoselective preparation of 2-substituted succinic acid deriv Stereoselective preparation of 2-substituted succinic acid deriv

1996-12-17

1998-09-15

Davis, Zinna Northington

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548194, 560183, C07D27720, C07C 1901, C07C 19075

Patent

active

058080856

ABSTRACT:
A highly efficient and practical means has been developed which enables compounds of the formula: ##STR1## wherein R.sup.1 is lower alkoxy, lower alkylamino, di-(loweralkyl) amino, or the monovalent radical A--NR.sup.3, wherein A is lower alkyl or A is R.sup.4 R.sup.5 NC(O)CH.sub.2 wherein, for example, R.sup.4 is hydrogen or alkyl and R.sup.5 is hydrogen, alkyl or a substituted alkyl, or R.sup.5 is R.sup.6 R.sup.7 N-Alk wherein R.sup.6 and R.sup.7 each is hydrogen or lower alkyl and Alk is a divalent alkyl radical; R.sup.3 is, for example, benzyl, alkyl or a substituted alkyl; and R.sup.2 is, inter alia, alkyl, cycloalkyl, 1H-imidazol-4-yl, 4-thiazolyl or 2-amino-4-thiazolyl; to be prepared through the kinetic resolution of a compound of the formula: ##STR2## wherein R.sup.1 is as defined herein, R.sup.2 is as defined herein, and B is lower alkyl. These compounds are useful intermediates in the synthesis of renin inhibiting compounds.

REFERENCES:
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J. Chem. Soc. Perkin Trans, 1, 1990, pp. 1441-1445, "Asymmetric Synthesis of (R)-and (S)-4-(Substituted Benzyl)dihydrofuran-2(3H)-ones: An Application of theRuthenium-binap+Complex-catalysed Asymmetric Hydrogenation ofAlkylidenesuccinic Acids", L. Shao et al.
Journal of the American Chemical Society, 90:13, Jun. 19, 1968, pp. 3495-3502, "Absolute Steric Course of Hydrolysis by .alpha.-Chymotrypsin. Esters of .alpha.-Benzylsuccinic, .alpha.-Methyl-.beta.-phenylpropionic, and .alpha.-Methylsuccinic Acids", S.G. Cohen and A. Milovanovic.

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