Process for the preparation of (2RS,3RS)-3-(2'-aminophenylthio)-

Details Process for the preparation of (2RS,3RS)-3-(2'-aminophenylthio)- Process for the preparation of (2RS,3RS)-3-(2'-aminophenylthio)-

1996-11-01

1998-05-26

Barts, Samuel

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

Organic compounds

Carboxylic acid esters

C07C14940

Patent

active

057568090

ABSTRACT:
(2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4"-methoxyphenyl)-propionic acid methyl ester, an important precursor for the preparation of the pharmaceutical active substance diltiazem, is obtained in a particularly high stereoselectivity and yield by addition of o-aminothiophenol onto 3-(4'-methoxyphenyl)-glycidic acid methyl ester if the reaction is carried out in the presence of alkali metal salts of weak acids in the presence of catalytic amounts of iron compounds.

REFERENCES:
patent: 4908469 (1990-03-01), Martin
Journal of the Chemical Society, Perkin Transactions 1, Nr. 3, Mar. 1985, Letchworth, GB, Seiten 421-427, XP002033505, T. Hashiyama, et al.: "Reaction of 3-phenylglycidic esters. Part 2. Stereo-and regioselectivity in the oxirane ring opening of methyl trans-3-(4-methoxyphenyl)glycidate with various thiophenols and the effects of solvent and temperature" * Seite 426, linke Spalte *.
T. Hashiyama, et al., Reaction of 3-Phenylglycidic Esters. Part 1.+ Stereoselective Opening of the Oxirane Ring of trans-3-Phenylglycidic Esters with 2-Nitrothiophenols and the Effect of Various Catalysts Thereon, J. Chem. Soc. Perkin Trans. I, pp. 1725-1732,(1984).
H. Kugita, et al., Synthesis of 1,5-Benzothiazepine Derivatives. I, Chem. Pharm. Bull., vol. 18, pp. 2028-2037,(1970).

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