Acetyl chloride → HCID 66700195, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl (2R,5R)-2-(aminocarbonyl)-5-[4-{[(2-fluorophenyl)methyl]oxy}-3-(methyloxy)phenyl]-2-[(methyloxy)methyl]-1-pyrrolidinecarboxylate (D65, 70 mg, 0.14 mmol) in a mixture of ethyl acetate (1.8 ml) and methanol (0.2 ml) at 0° C. was added AcCl (170 μl, 2.38 mmol). The mixture was stirred for 4 hours at room temperature. The solvent was evaporated and the residue was triturated with Et2O to afford the title compound as a white solid (49 mg, 82%); Rt (HPLC) 3.62 min; MS: (ES/+) m/z: 389 [MH]+ C21H25FN2O4 requires 388; 1H NMR (500 MHz, DMSO-d6) δ (ppm): 9.91-10.02 (br.s, 1H); 8.07-8.25 (br.s, 2H); 7.94-8.03 (br.s, 1H); 7.50 (t, 1H); 7.35-7.43 (m, 1H); 7.17-7.25 (m, 2H); 7.13 (s, 1H); 7.06 (d, 1H); 6.95 (dd, 1H); 5.08 (s, 2H); 4.51-4.66 (m, 1H); 3.92 (d, 1H); 3.74 (s, 3H); 3.69 (d, 1H); 3.26 (s, 3H); 2.17-2.35 (m, 2H); 1.97-2.12 (m, 1H); 1.79-1.96 (m, 1H).

Provenance & Evidence