Water → HCID 86713173, compound

Participants

Reaction Steps

(1R,2S)-2-amino-3-fluoro-1-(4-(3-(methylsulfonylmethyl)isoxazol-5-yl)phenyl)propan-1-ol (75 mg, 0.21 mmol) in dimethylformamide (2 mL) at 5° C. is treated with diisopropylethylamine (0.055 mL, 0.62 mmol) and then difluoroacetylchloride (0.026 mL, 0.25 mmol) is added and the mixture stirred at room temperature for 1 hour. Water is added (10 mL) and extracted with ethyl acetate (10 mL) and the organics washed with brine (10 mL), dried over MgSO4, filtered, concentrated and purified by reverse phase preparative HPLC to give the title compound (35 mg). 1H NMR (400 MHz, DMSO-d6) δ: 3.10 (s, 3H), 4.33 (m, 1H), 4.40-4.60 (m, 1H), 4.65-4.80 (m, 3H including 2H singlet at 4.75), 4.92 (bs, 1H), 6.17 (t, 1H), 7.08 (s, 1H), 7.51 (d, 2H), 7.86 (d, 2H), 8.80 (d, 1H); m/z (Cl) 407 [M+H].

Provenance & Evidence