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

Participants

Reaction Steps

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

Provenance & Evidence