Methanol → N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-dihydro-2-benzofuran-5-yl)acetyl]thiophene-3-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-{2-[(6-methyl-1,3-dihydro-2-benzofuran-5-yl)methyl]-1,3-dithian-2-yl}thiophene-3-sulfonamide described in Production Example 1-7 (300 mg, 0.55 mmol), methanol (20 mL), water (2 mL) and silver nitrate (940 mg, 5.5 mmol) was stirred for 3 days at 55° C. The reaction mixture was allowed to cool to room temperature, tetrahydrofuran (40 mL) and brine (1 mL) were added at that temperature, and the mixture was filtered with Celite. The filtrate was extracted by addition of ethyl acetate (200 mL), water (100 mL) and saturated aqueous citric acid solution (1 mL). The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:9), and then further purified by silica gel thin-layer chromatography (methanol:ethyl acetate=1:32) to give the title compound (45 mg, 18% yield).

Provenance & Evidence