HCID 9863761, compound → HCID 21958068, compound

Participants

Reaction Steps

To a solution of ethyl 6-[N-(4-chloro-2-fluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate obtained in Example 1 (Compound 1, 250 mg) in methanol (5 ml), concentrated sulfuric acid (0.2 ml) was added and the mixture was stirred under reflux for 8 days hours. The reaction mixture was concentrated under reduced pressure and diluted with ethyl acetate (30 ml) and washed with water (30 ml). The ethyl acetate layer was washed with water (30 ml×2) and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was ,subjected to silica gel chromatography (eluent: ethyl acetate/hexane=1/4) and desired fractions were concentrated under reduced pressure. The residue was purified by an ODS column chromatography (eluent: methanol/water=4/1) and then crystallized from diisopropyl ether to yield methyl 6-[N-(4-chloro-2-fluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (Compound 24, 58 mg) as colorless prism-like crystals.

Provenance & Evidence