Hydrochloric Acid → 3-(2-Fluoro-4-[(4-{[[2-(2-fluorophenyl)ethyl](4-isopropyl-1,3-thiazol-2-yl)amino]methyl}benzyl)oxy]phenyl}-propanoic acid

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Reaction Steps

To a solution of N-[2-(2-fluorophenyl)ethyl]-4-isopropyl-1,3-thiazole-2-amine (139 mg) in N,N-dimethylformamide (2 mL) was added sodium hydride (20 mg), and the mixture was stirred at room temperature for 1 hr. Ethyl 3-(4-{[4-(chloromethyl)benzyl]oxy}-2-fluorophenyl)propanoate (175 mg) was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:1 in volume ratio) to give a yellow oil. This oil was dissolved in ethanol (5 mL), 2N aqueous sodium hydroxide solution (2 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with water, neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.) and concentrated to give the title compound (206 mg, yield 71%) as a yellow oil.

Provenance & Evidence