Methanol → Methyl (2S)-2-amino-3-(3,4-dimethoxyphenyl)propanoate

Participants

Reaction Steps

Thionyl chloride (3.2 g, 2.0 mL, 26.8 mmol) was added dropwise to a suspension 3-(3,4-dimethoxyphenyl)-L-alanine 1 (2.0 g, 8.9 mmol) in anhydrous MeOH (50 mL) at 0° C. under a nitrogen blanket. The mixture was slowly warmed to room temperature, then stirred for 72 hours. The solvent was removed under reduced pressure to provide a solid. The crude product was taken up in CH2Cl2, then washed with saturated NaHCO3 and saturated NaCl. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to yield a light brown oil (1.97 g, 93%).

Provenance & Evidence