4-Fluorobenzoic Acid → HCID 58235429, compound

Participants

Reaction Steps

1-(3-Dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (68.0 mg, 0.35 mmol) was added to a solution of (S)—O-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yl)hydroxylamine (100 mg, 0.32 mmol), 1-hydroxybenzotriazole (45.0 mg, 0.35 mmol), 4-fluorobenzoic acid (45 mg, 0.32 mmol) and N,N-diisopropylethylamine (125 mg, 0.97 mmol) in N,N-dimethylformamide (10 m1). The reaction mixture was stirred at room temperature for 17 hours and quenched with H2O (30 ml). The aqueous phase was extracted with ethyl acetate (30 ml×3) and the combined organic phase was washed with aqueous 0.1 N HCl solution (20 ml), H2O (30 ml×3) and brine (30 ml), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/hexane: 33/67) to give (S)-2-(4-fluorophenyl)-N-(1-(3-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yloxy)acetamide (90.0 mg, 65%) as a white solid: LCMS: 433 [M+1]+. 1H NMR (DMSO-d6) δ: 1.88 (m, 1H), 2.04 (m, 1H), 3.37 (m, 3H), 3.54 (d, 1H), 4.55 (s, 1H), 7.29 (t, 2H), 7.76 (m, 2H), 7.87 (t, 1H), 8.06 (t, 2H), 8.15 (d, 1H), 11.6 (s, 1H).

Provenance & Evidence