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

Participants

Reaction Steps

To a solution of tert-butyl [6-(hydroxymethyl)pyridin-2-yl]carbamate (252 mg, 1.12 mmol) in acetonitrile (2.5 mL) and diisopropylethylamine (0.59 mL, 3.4 mmol) was added methanesulfonyl chloride (0.094 mL, 1.2 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 additional hours. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and the mixture was extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford {6-[(tert-butoxycarbonyl)amino]pyridin-2-yl}methyl methanesulfonate that was used without further purification. MS ESI calc'd for C12H19N2O5S [M+H]+ 303. found 303.

Provenance & Evidence