Triethylamine → 2-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid

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Reaction Steps

A solution of triethylamine (0.75 mL, 5.4 mmol) in N,N-dimethylformamide (2.0 mL) was added to a solution of 4-bromomethyl-2-tert-butoxycarbonylaminopyridine (Reference compound No. 8-1, 500 mg, 1.7 mmol) and 2-mercaptonicotinic acid (270 mg, 1.7 mmol) in N,N-dimethylformamide (3.0 mL) under ice-cooling, and the mixture was stirred for 12 hours at room temperature. Ethyl acetate (20 mL) was added to the reaction mixture, and the whole was extracted with 0.1N aqueous sodium hydroxide solution (50 mL). 1N Hydrochloric acid was added to the aqueous layer to adjust to pH 5, and the precipitated crystal was filtered off. The crystal was dried under reduced pressure at 60° C. to give 560 mg of the title reference compound as a colorless crystal. (Yield 88%)

Provenance & Evidence