Hydrochloric Acid → Methyl 6,6,7,7,7-pentafluoro-5-methyl-2-(3,3,3-trifluoropropylsulfonyl)heptanoate

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To a solution of 2.0 g of 4,4,5,5,5-pentafluoro-3-methyl-pentyl methanesulfonate and 1.7 g of methyl (3,3,3-trifluoropropylsulfonyl)acetate in 50 ml of dimethyl sulfoxide was added 1.0 g of potassium carbonate at room temperature, heated to 60° C. and then stirred at the same temperature for 7 days. The reaction mixture was allowed to stand to cool to nearly room temperature. To the reaction mixture was added 10% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.5 g of methyl 6,6,7,7,7-pentafluoro-5-methyl-2-(3,3,3-trifluoropropylsulfonyl)heptanoate, which was dissolved in 20 ml of tetrahydrofuran. To the solution was added 0.1 g of sodium hydride (60% in oil) at room temperature. The reaction mixture was stirred at the same temperature for 0.5 hours. To the reaction mixture was added 0.2 g of N-chlorosuccinimide at room temperature, and then stirred for 2 hours. Thereto was added 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was dissolved in 20 ml of methanol. To the solution was added 0.5 ml of ammonia (7M methanol solution) at room temperature, and then stirred at the same temperature for 30 hours. The reaction mixture was concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 0.22 g of 2-chloro-6,6,7,7,7-pentafluoro-5-methyl-2-(3,3,3-trifluoropropylsulfonyl)heptanamide (hereinafter referred to as the present compound (31)).

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