O-Xylene → (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide

Participants

Reaction Steps

A mixture of (2R,3S)-3-(4-methoxyphenyl)glycidamide (1.93 g) and xylene (15 ml) is refluxed under nitrogen atmosphere. To the reaction solution is added a solution of 2-aminothiophenol (1.38 g) and iron sulfate·heptahydrate (0.28 mg) in methanol (0.2 ml) immediately after the refluxing starts. After reaction at the same temperature for 5 minutes, the reaction solution is cooled to room temperature. The reaction solution is subjected to HPLC analysis to confirm the production of 3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionamide (2.69 g) (threo/erythro=91/9). The reaction solution is concentrated under reduced pressure to remove the solvent, and the residue thus obtained is dissolved with heating in ethanol (3 ml) and water (3 ml). The solution is gradually cooled with stirring to 0° C. for crystallization. The precipitated crystals are collected by filtration. The collected crystals are washed with iced 50% ethanol, and dried at 50° C. to give (2S,3S)-3-(2-aminophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propioamide (0.84 g).

Provenance & Evidence