Acetyl chloride → HCID 66700844, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl (2S,5S)-2-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (D79, 130 mg, 0.295 mmol) in a mixture of ethyl acetate (2.7 ml) and methanol (0.3 ml) at 0° C. was added AcCl (130 μl, 1.82 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 (80 mg, 82%); Rt (HPLC) 3.60 min; MS: (ES/+) m/z: 341 [MH+] C20H21FN2O2 requires 340; 1H NMR (500 MHz, DMSO-d6) δ(ppm): 10.37 (br. s, 1H), 8.78 (br. s, 1H), 8.42 (s, 1H), 7.53-7.58 (m, 1H), 7.54 (d, 2H), 7.42 (dd, 1H), 7.25 (t, 1H), 7.23 (t, 1H), 7.10 (d, 2H), 5.13-5.21 (m, 2H), 4.65-4.76 (m, 1H), 3.25-3.33 (m, 2H), 2.48-2.55 (m, 1H), 2.31-2.42 (m, 2H), 2.27-2.34 (m, 2H), 2.04-2.14 (m, 1H).

Provenance & Evidence