Potassium Carbonate → (S)-4-nitrophenyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethylcarbamate

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Reaction Steps

To a solution of (S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethanamine (200 mg, 0.45 mmol) in DCM (2 mL) was added 4-nitrophenyl carbonochloridate (226.9 mg, 1.13 mmol) followed by the addition of K2CO3 (620.6 mg, 4.5 mmol). The reaction mixture was stirred at room temperature for 18 h and filtered through a small silica pad. The filtrate was diluted with DCM (20 mL), washed with saturated NaHCO3 (8×15 mL) till the aqueous layer only showed light yellow color. The organic layer was dried over MgSO4, filtered and concentrated to give (S)-4-nitrophenyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethylcarbamate as a yellow oil (273 mg, crude 100%). This yellow oil was used directly to the next step without further purification. LCMS RT=2.213 min [M+H] 607.94 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 2 minutes containing 0.1% TFA; 5 mL/min, monitoring at 220 nm)

Provenance & Evidence