Acetyl chloride → HCID 68411334, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(2-fluoro-4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-pyrrolidinecarboxylate (D47, 130 mg, 0.300 mmol) in a mixture of ethyl acetate (2.3 ml) and methanol (0.230 ml) was added acetyl chloride (64 μl, 2.5 eq) at 0° C. The mixture was shaken for 2 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 (101 mg, 92%); Rt (HPLC): 3.66 min; MS: (ES/+) m/z: 333 [MH+], C18H18F2N2O2 requires 332; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.36 (br. s., 1H), 8.35 (br. s., 1H), 8.04 (s, 1H), 7.72 (s, 1H), 7.51-7.64 (m, 2H), 7.40-7.49 (m, 1H), 7.20-7.32 (m, 2H), 7.05 (dd, 1H), 6.98 (dd, 1H), 5.19 (s, 2H), 4.81 (dd, 1H), 4.31 (dd, 1H), 2.22-2.42 (m, 2H), 2.01-2.22 (m, 2H).

Provenance & Evidence