Methanol → HCID 67397796, compound

Participants

Reaction Steps

tert-Butyl ({5-(2-fluoropyridin-3-yl)-1-[(3-methoxyphenyl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (303 mg) was dissolved in ethyl acetate (1 mL) and methanol (1 mL) and 4 mol/L hydrogen chloride-ethyl acetate solution (3 mL) were added. The mixture was stirred at room temperature for 2 hr, and concentrated under reduced pressure. 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 the title compound as a free base (149 mg). A solution of the obtained free base (149 mg) in ethyl acetate (2 mL) was added to a solution of fumaric acid (46 mg) in methanol (2 mL), and the mixture was concentrated under reduced pressure. The obtained crystals were recrystallized from a mixed solvent of ethanol-water=9:1 to give the title compound as colorless crystals (yield 138 mg, 44%).

Provenance & Evidence