Triethylamine → HCID 54570052, compound

Participants

Reaction Steps

To a stirred solution of 3-nitrophenylacetic acid (10 g, 0.055 mol), glycine methyl ester hydrochloride (7.3 g, 0,058 mol), triethylamine (8.0 ml, 0.058 mol) and 4-dimethylaminopyridine (7.1 g, 0,058 mol) in dichloromethane (200 ml) was added, under nitrogen, 1-(3-dimethylaminopropyl )-3-ethylcarbodiimide(11.1 g, 0.058 mol), the mixture was stirred at room temperature for 18 h then the solvent removed in vacuo. Ethyl acetate (300 ml) was added to the residue and the mixture partitioned with 1M hydrochloric acid (2×200 ml), saturated sodium bicarbonate solution (2×200 ml), water (100 ml) and brine (100 ml). The organic phase was separated then evaporated in vacuo. The residue was triturated with ether (200 ml) to afford the desired amide (12.5 g, 90%) as a white solid. mp 104°-105° C. 1H NMR (360MHz, CDCl3) δ3.71 (2H, s), 3.76 (3H, s), 4.06 (2H, d, J 5Hz), 6.06 (1H, br s), 7.53 (1H, dd, J=8 and 8Hz), 7.67 (1H, d, J =8Hz), 8.16 (2H, m).

Provenance & Evidence