Ethyl Acetate → HCID 68411867, compound

Participants

Reaction Steps

tert-Butyl ({4-(2-fluorophenyl)-5-[(3-methoxyphenyl)sulfinyl]-2-thienyl}methyl)methylcarbamate (231 mg) was dissolved in ethyl acetate (3 mL) and ethanol (1 mL), and a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added at room temperature. After stirring for 4 hr, the reaction mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane-ethyl acetate=1:1→1:9) to give a free base of the title compound (155 mg) as a pale-yellow oil. To a solution of fumaric acid (50 mg) in ethanol (10 mL) was added a solution of the obtained free base in ethyl acetate (5 mL), and the solvent was evaporated under reduced pressure. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and 2-propanol to give the title compound as a white powder (yield 118 mg, yield 50%).

Provenance & Evidence