Methanesulfonyl chloride → (6-(Tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate

Participants

Reaction Steps

To a solution of tert-butyl 6-(hydroxymethyl)pyridin-2-ylcarbamate (93; 3.0 g, 13.4 mmol) and DIPEA (5.0 g, 40 mmol) in acetonitrile (30 mL) was added MsCl (2.0 g, 17.4 mmol) over a period of 30 min at 0° C. and the mixture was stirred for 2 h at room temperature. The reaction was quenched by adding saturated aqueous NaHCO3 and extracted with ethyl acetate (3×60 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford essentially quantitative yield of crude (6-(tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate 94.

Provenance & Evidence