Methanol → (S)-(+)-2-Phenylglycine methyl ester hydrochloride

Participants

Reaction Steps

To a stirred solution of D-phenylglycine (11) (20 g, 132 mmol) in methanol (100 ml) at -10° C. was added thionyl chloride (10.62 ml, 146 mmol) and the solution was refluxed for 2 hours. After concentration in vacuo the product was recrystallised from methanol-diethyl ether mixture to give the title compound (12) (26.6 g, 100%); δH (D2O; 200 MHz) 2.95-3.18 (2H, m, CH2CH), 3.62 (3H, s, CH3), 4.21 (1H, dd, J=6.1 and 7.4, CH2CH), 4.59 (2H, s, NH2), 7.06-7.27 (5H, m, ArCH).

Provenance & Evidence