Dimethylamine, hydrochloride → tert-Butyl 6-[({4'-[2-(dimethylamino)-2-oxoethyl]-1,1'-biphenyl-4-yl}oxy)methyl]-2-hydroxy-3-(trifluoromethyl)benzoate

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Reaction Steps

Dimethylamine hydrochloride (41 mg, 0.502 mmol), N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (96 mg, 0.50 mmol), hydroxybenzotriazole (77 mg, 0.50 mmol) and triethylamine (0.10 ml) were added to a solution of (4′-{[2-(tert-butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetic acid (168 mg, 0.334 mmol) obtained in Example (7) in acetonitrile (10 ml). After the mixture was stirred for 10 hours, a saturated aqueous ammonium chloride solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=3/1-methylene chloride/methanol=15/1) to give the title compound as a pale yellow crystal (303 mg, yield: 34%).

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