Acetyl chloride → HCID 68410011, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl (2R,5S)-2-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-5-[(methylamino)carbonyl]-1-pyrrolidinecarboxylate (D96, 40 mg, 0.09 mmol) in ethyl acetate (0.9 ml) and methanol (0.1 ml) at 0° C. was added AcCl (40 μl, 0.56 mmol) and the mixture was stirred for two hours at room temperature. The solvent was removed under nitrogen flow and the residue triturated with Et2O. The solvent was removed to afford the title compound as a white solid (28 mg, 85%). Rt (HPLC): 3.74 min; MS: (ES/+) m/z: 329-[MH+] C19H21FN2O2 requires 328; 1H NMR (500 MHz, DMSO-d6) δ (ppm): 10.03-10.78 (br.s, 1H); 8.56 (q, 1H); 7.95-8.46 (br.s, 1H); 7.55 (dt, 1H); 7.49 (d, 2H); 7.39-7.46 (m, 1H); 7.20-7.29 (m, 2H); 7.09 (d, 2H); 5.16 (s, 2H); 4.58 (dd, 1H); 4.28 (dd, 1H); 2.70 (d, 3H); 2.21-2.37 (m, 2H); 1.98-2.17 (m, 2H).

Provenance & Evidence