4-Toluenesulfonyl chloride → trans-N-[2-(4-Phenylethynylbenzamido)benzenesulfonyl]-3-hexenamide

Participants

Reaction Steps

In a stream of nitrogen and at 0° C., 249 mg (1.30 mmol) of tosylic chloride was added to an anhydrous tetrahydrofuran (10 ml) solution containing 149 mg (1.30 mmol) of 3-hexenoic acid and 532 mg (4.35 mmol ) of 4-dimethylaminopyridine, and the mixture was stirred for 1 hour. Next, this was mixed with 300 mg (0.80 mmol) of 4-phenylethynyl-N-(2-sulfamoylphenyl)benzamide produced in Reference Example 10 and stirred at room temperature for 1 hour, and then the solvent was evaporated under a reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with water, a potassium hydrgensulfate aqueous solution and saturated brine in that order and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was purified by a silica gel chromatography to obtain 250 mg (yield: 65.0%) of the title compound.

Provenance & Evidence