Methanol → Methyl 2-amino-3-(3,5-difluorophenyl)propanoate hydrochloride

Participants

Reaction Steps

To a stirred suspension of DL-3,5-difluorophenylalanine (3.00 g, 14.9 mmol) in anhydrous methanol (30 mL) was added dropwise thionyl chloride (1.64 mL, 22.5 mmol) at 0° C. The resulting solution was refluxed for 18 hours, cooled to ambient temperature and concentrated in vacuo to dryness. The residue was triturated with diethyl ether to give methyl 2-amino-3-(3,5-difluorophenyl)propanoate hydrochloride as a colorless crystalline solid (3.68 g, 98%): 1H NMR (300 MHz, CD3OD) δ 6.93-6.84 (m, 3H), 4.34 (dd, J=7.4, 6.3 Hz, 1H), 3.78 (s, 3H), 3.30-3.09 (m, 2H).

Provenance & Evidence