Hydrochloric Acid → 3182-88-5

Participants

Reaction Steps

A mixture of isobutylamine (0.90 mL, 0.0091 mol), bromoacetic acid, ethyl ester (1.0 mL, 0.0090 mol), and triethylamine (1.28 mL, 0.00918 mol) in diethylether (15 mL) was stirred at room temperature for 24 hours. The resulting suspension was filtered off and washed with diethylether. The filtrate and washings were combined and rotary evaporated to an oil. The oil was chromatographed on silica gel (150 g, 230-400 mesh) eluting with dichloromethane-diethylether (19:1, 8×125 mL; 15:1, 7×125 mL; 10:1, 15×125 mL). Fractions containing product were combined and rotary evaporated to give an oil. The oil was dissolved in diethylether, concentrated hydrochloric acid (0.52 mL, 0.0063 mol HCl) was added, and the volatiles were rotary evaporated to give a white solid. The solid was dried in vacuo; yield 1.0 g (59%). 1H-NMR (DMSO-d6): δ9.23 (br s, 2H), 4.22 (q, 2H), 3.96 (m, 2H), 3.41 (br s, H2O), 2.78 (m, 2H), 2.00 (m, 1H), 1.25 (t, 3H), 0.94 (d, 6H).

Provenance & Evidence