Patent ID: 6365754
Filing Date: 2002-04-02
Classification: C07C,C07D

Abstract:
A process for producing an erythro-3-amino-2-hydroxybutyric acid derivative characterized in that a 2-aminoaldehyde derivative represented by the general formula [I](wherein R1 is a straight-chained, branched or cyclic alkyl group having one to six carbon atoms, an alkylthio group or an arylthio group having one to eight carbon atoms, or a substituted or unsubstituted aryl group, P1 and P2 are, the same or different, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aralkyloxycarbonyl group, a substituted or unsubstituted arylcarbonyl group, or a substituted or unsubstituted arylsulfonyl group, or P1 and P2 may together represent a substituted or unsubstituted phthaloyl or naphthaloyl ring) is reacted with a metal cyanide in the presence of an acid chloride and/or an acid anhydride or reacted with an organic cyanide in the presence of a Lewis acid to give stereoselectively an erythro-3-amino-2-hydroxybutyronitrile derivative represented by the general formula [II](wherein R1, P1 and P2 are the same as mentioned above, and R2 is an alkylcarbonyl group, or a substituted or unsubstituted arylcarbonyl group), and then the nitrile derivative is treated with an acid in water or in a water-containing solvent to convert it into an erythro-3-amino-2-hydroxybutyric acid derivative represented by the general formula [III](wherein R1 is the same as mentioned above, R3 is hydrogen, Q1 and Q2 are, the same or different, hydrogen, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted arylsulfonyl group, or Q1 and Q2 may together represent a substituted or unsubstituted phthaloyl or naphthaloyl ring), or the nitrile derivative is treated with an acid in an alcoholic solvent represented by the general formula or R3OH to convert it into an ester of butyric acid represented by the above general formula [III] (in each formula, R1, Q1 and Q2 are the same as mentioned above, and R3 is a straight-chain, branched or cyclic alkyl group having one to six carbon atoms, or a substituted or unsubstituted aralkyl group).