Optical resolution of threo-2-hydroxy-3-(2-aminophenylthio)-3-(4

Details Optical resolution of threo-2-hydroxy-3-(2-aminophenylthio)-3-(4 Optical resolution of threo-2-hydroxy-3-(2-aminophenylthio)-3-(4

1993-07-12

1994-04-12

Prescott, Arthur C.

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

Organic compounds

Carboxylic acid esters

560 17, 562401, 562402, 562431, C07C31928, C07B 5700

Patent

active

053027418

ABSTRACT:
D(+)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)propionic acid, an important intermediate in the synthesis of diltiazem hydrochloride, is obtained in better yields and high optical purity by a novel resolution process comprising the reaction of 2 moles of the (.+-.) racemic acid with 1 mole of quinine and 1 mole of a base in a suitable polar solvent system to form a salt of the D(+) acid and quinine which precipitates; separating said salt and decomposing it with a strong base.

REFERENCES:
patent: 4552695 (1985-11-01), Igarashi et al.
patent: 5008411 (1991-04-01), Coffen et al.
patent: 5097059 (1992-03-01), Giordano et al.
patent: 5183922 (1993-02-01), Rizzi et al.
Jacques, Jean et al., "Enantiomers, Racemates and Resolutions", 1981, John Wiley & Sons, New York, Brisbane, Chickester, Toranto, pp. 307-312.

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