Benzyl Alcohol → HCID 70945575, compound

Participants

Reaction Steps

To crude 2-(5-bromopyridin-3-yl)-3-(tert-butyldimethylsilyloxy)-3-(2,5-difluorophenyl)-2-methylpropanoic acid (450 mg, 0.925 mmol) in toluene (12 mL) was added benzyl alcohol (0.096 mL, 0.925 mmol), triethylamine (0.258 mL, 1.850 mmol) and diphenyl phosphorazidate (0.200 mL, 0.925 mmol). The mixture was placed in a heat bath set to 60° C. for 18 h, concentrated and purified via preparative liquid chromatography (Sunfire C18 OBD 30×100 mm 5 μm, A=95% H2O/5% Acetonitrile, B=95% Acetonitrile/5% H2O, Modifier 10 mM Ammonium Acetate, 0.00 min=0% B, 8.0 min=100% B, 13.0 min=100% B, Flow rate=40 mL/min) providing 80 mg (15%) benzyl 2-(5-bromopyridin-3-yl)-1-(tert-butyldimethylsilyloxy)-1-(2,5-difluorophenyl)propan-2-ylcarbamate. Mass Spectral Anal. Calcd. for [M+H]+ C28H33BrF2N2O2Si: 591.1. found 590.0.

Provenance & Evidence