Acetyl chloride → HCID 68411591, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-{3-[(phenylmethyl)oxy]phenyl}-1-pyrrolidinecarboxylate (D54, 142 mg, 0.358 mmol) in a mixture of ethyl acetate (2.3 ml) and methanol (0.23 ml) was added acetyl chloride (64 μl, 2.5 eq) at 0° C. The mixture was shaken for 1.5 h and slowly allowed to warm to room temperature. After evaporating the solvent, the residue was triturated with diethyl ether to afford the title compound as a white solid (71 mg, 60%); Rt (HPLC): 3.51 min. MS: (ES/+) m/z: 297 [MH+], C18H20N2O2 requires 296; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.52 (br. s., 1H), 8.41 (br. s., 1H), 8.03 (s, 1H), 7.73 (s, 1H), 7.31-7.50 (m, 6H), 7.26 (t, 1H), 7.10 (d, 1H), 7.06 (dd, 1H), 5.13 (s, 2H), 4.62 (dd, 1H), 4.32 (dd, 1H), 2.24-2.44 (m, 2H), 2.09-2.23 (m, 1H), 1.93-2.09 (m, 1H).

Provenance & Evidence