m-Chloroperbenzoic acid → HCID 69480155, compound

Participants

Reaction Steps

To a cold (0° C.) solution of 30% ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methylthio)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and 70% ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methylsulfinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (269 mg, 0.611 mmol) in dichloromethane (10 mL) was added m-chloroperoxybenzoic acid (158 mg, 0.915 mmol). The reaction mixture was warmed to room temperature and stirred 3 hours. The reaction mixture was diluted with dichloromethane and washed with water and brine, then dried over sodium sulfate. Filtration and concentration provided ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-[3-(methylsulfonyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.55 (s, 1 H), 7.66 (s, 1 H), 7.22 (dd, J=8.5, 5.5 Hz, 2 H), 7.03 (t, J=8.5 Hz, 2 H), 4.52 (q, J=7.1 Hz, 2 H), 4.39 (t, J=7.8 Hz, 2 H), 4.13 (s, 2 H), 3.16 (t, J=6.9 Hz, 2 H), 2.95 (s, 3 H), 2.22 (m, 2 H), 1.48 (t, J=7.0 Hz, 3 H); MS m/z 461 (M−H)−.

Provenance & Evidence