Water → (3R)-4-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)-1-(3-cyano-5-fluorophenyl)butyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl ((2R)-2-((tert-butyldimethylsilyl)oxy)-4-(3-cyano-5-fluorophenyl)-4-hydroxybutyl)carbamate (I-10) (5.3 g, 12.1 mmol) in DCM (50 mL) at −60° C. was added TEA (5.1 mL, 36.3 mmol) and MsCl (0.98 mL, 12.2 mmol). The resulting mixture was stirred at −60° C. for 2 hours. The reaction was poured into water, diluted with DCM and washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography on silica gel with EtOAc/hexanes gradient as eluant to yield (3R)-4-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)-1-(3-cyano-5-fluorophenyl)butyl methanesulfonate (I-11). MS m/z 539.1 (M+23)+. Compound decomposed on standing. Used immediately in next reaction without delay.

Provenance & Evidence