Acetyl chloride → HCID 68408593, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-[(phenylmethyl)oxy]phenyl)-1-pyrrolidinecarboxylate (D12, 45 mg, 0.113 mmol) in a mixture of ethyl acetate and methanol (9/1, 1 ml) was added acetyl chloride (20 μl, 0.282 mmol) at 0° C. The mixture was shaken for 1.5 h and slowly allowed to warm to room temperature. After 4 h under these conditions, additional acetyl chloride (20 μl, 0.654 mmol) was added. After evaporating the solvent, the residue was triturated with diethyl ether to afford the title compound as a white solid (25 mg, 66%); Rt (HPLC): 3.55 min; 1H NMR (300 MHz, DMSO-d6) δ (ppm): 10.50 (bs, 1H); 8.15 (bs, 1H); 8.05 (s, 1H); 7.73 (s, 1H); 7.42-7.49 (m, 4H); 7.40 (t, 2H); 7.30-7.36 (m, 1H); 7.08 (d, 2H); 5.15 (s, 2H); 4.60 (dd, 1H); 4.30 (dd, 1H); 2.23-2.40 (m, 2H); 2.10-2.20 (m, 1H); 1.95-2.08 (m, 1H).

Provenance & Evidence