Methanesulfonyl chloride → HCID 57947555, compound

Participants

Reaction Steps

To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) followed by DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min and diluted with DCM (300 mL). The organic mixture washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was then dissolved in DMF (20.0 mL). To the resulting solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated at 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT and added water (20 mL) and EtOAc (200 mL). The organic layer was separated, washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps).

Provenance & Evidence