Methane → HCID 58235363, compound

Participants

Reaction Steps

A solution of (S)—O-(1-(4-(trifluoromethoxy)phenylsulfonyl)pyrrolidin-3-yl)hydroxylamine (250 mg, 0.76 mmol) in tetrahydrofuran (10 ml) was added over 30 minutes to a suspension of trichloromethyl chloroformate (227 mg, 1.15 mmol) and activated charcoal (20 mg) in tetrahydrofuran (35 ml) at 0° C. over 30 minutes. After stirring at room temperature for 18 hours, the reaction mixture was filtered over silicagel and the filtrate was concentrated in vacuo. The residue was dissolved in tetrahydrofuran (15 ml), 4-fluoroaniline (93.6 mg, 0.84 mmol) and N,N-diisopropylethylamine (296 mg, 2.3 mmol) were added and the whole was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate (50 ml), washed with H2O (20 ml×2), brine (20 ml×2), dried over Na2SO4 and concentrated in vacuo. The residual solid was recrystallized from diethyl ether to give (S)-1-(4-fluorophenyl)-3-(1-(4-(trifluoromethoxy)phenylsulfonyl)pyrrolidin-3-yloxy)urea as a white solid (127 mg, 36%): LCMS: 464 [M+1]+. 1H NMR (DMSO-d6) δ: 1.85 (m, 1H), 2.09 (m, 1H), 3.25 (m, 3H), 3.53 (d, 1H), 4.36 (s, 1H), 7.07 (t, 2H), 7.47 (d, 2H), 7.56 (d, 2H), 7.92 (d, 2H), 8.63 (s, 1H), 9.45 (s, 1H).

Provenance & Evidence