Hydrochloric Acid → HCID 178475073, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.6M hexane solution, 11.4 mL) was added dropwise to a mixture of tert-butyl (6-(((2S)-2-acetamidopropyl)oxy)-5-fluoropyridin-3-yl)carbamate (1.70 g) and THF (20 mL) at −78° C. under an argon atmosphere, and the obtained mixture was stirred at −78° C. for 1 hr. To the reaction mixture was added trimethyl borate (2.36 mL), the obtained mixture was allowed to warm to room temperature, and stirred at room temperature overnight. The reaction mixture was cooled to 0° C., and a mixture of 8M aqueous sodium hydroxide solution (2.60 mL) and aqueous hydrogen peroxide (30%, 5 mL) were added thereto. The obtained mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium thiosulfate solution at 0° C., and the mixture was acidified with 6M hydrochloric acid, and extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.541 g).

Provenance & Evidence