Phenylmethanesulfonyl chloride → 3-Benzylsulfonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Participants

Reaction Steps

To a solution of tert-butyl 2-[3-amino-6-methyl-2-oxo-1(2H)-pyridinyl]acetate (3.04 g, 12.1 mmol) in pyridine (30 mL) cooled to 0° C. was added benzylsulfonylchloride (2.67 g, 15.1 mmol). While stirring of the reaction mixture the precipitate formed. After one hour the solvent was evaporated under reduced pressure and the product was partitioned between dichloromethane and 10% KHSO4 solution. The aqueous phase was extracted with dichloromethane twice. The combined organic phases were dried over a drying agent and the solvent was evaporated under reduced pressure. A brown-reddish product obtained was suspended in ethyl acetate and heated to reflux, then cooled and filtered to give 2.56 g (6.52 mmol) of a pink product.

Provenance & Evidence