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

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).

1. temperatureis refluxed
2. temperaturewith heating under nitrogen atmosphere
3. customthe mixture is reacted at the same temperature for 5 minutes
4. concentrationThe reaction mixture is concentrated under reduced pressure
5. customto remove the solvent
6. dissolutionthe residue is dissolved
7. temperaturewith heating in ethanol (3 ml)
8. temperatureThe mixture is gradually cooled to 0° C.
9. filtrationThe precipitated crystals are collected by filtration
10. washwashed
11. temperaturewith chilled 50% ethanol
12. customdried at 50° C.

ORD record

ord-c21abbfe19f044938f2de66d89653dae

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05847122