Hydrochloric Acid → 2-((4-Chlorophenyl)formamido)propanoic acid

Participants

Reaction Steps

To a solution of L-Alanine (2.67 g, 30.0 mmol) and KOH (3.90 g, 69.5 mmol) in water (50.0 mL) was added 4-chlorobenzoyl chloride (5.25 g, 30.0 mmol). After stirring at RT for 16H, the reaction mixture was cooled to 0° C., acidified to pH=2 with 10 M HCl and extracted with EtOAc (3×75 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, concentrated and air dried under vacuum to afford 5.80 g (85% yield) of the title compound as a white solid that was carried forward without further purification: 1H NMR (500 MHz, DMSO-d6) δ 12.62 (1H, br. s.), 8.76 (1H, d, J=7.15 Hz), 7.90 (2H, d, J=8.25 Hz), 7.55 (2H, d, J=8.25 Hz), 4.40 (1H, qd, J=7.33, 7.15 Hz), 1.38 (3H, d, J=7.15 Hz); HPLC retention time: 2.223 min; LCMS (ES): m/z 228 [M+H]+.

Provenance & Evidence