Hydrochloric Acid → HCID 69423782, compound

Participants

Reaction Steps

Tetrakis(triphenolphosphine)palladium (120 mg) was added to a mixture of ethyl 3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-trifluoromethanesulfonyloxy-1H-pyrazol-4-yl]propionate (1.20 g), 4-trifluoromethylphenylboronic acid (0.46 g), 2N aqueous sodium carbonate solution (2.6 ml), ethanol (3 ml), and toluene (50 ml). This mixture was refluxed under an argon atmosphere for 13 hours. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatography, and a colorless oily substance was obtained from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). A mixture of the oily substance obtained, 1N aqueous sodium hydroxide solution (5 ml), ethanol (5 ml) and tetrahydrofuran (5 ml) was stirred at room temperature for 2 hours. The reaction mixture was acidified with dilute hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The colorless crystals obtained were collected by filtration to yield 3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(4-trifluoromethylphenyl)-1H-pyrazol-4-yl]propionic acid (250 mg, yield: 22%). This was recrystallized from ethyl acetate-hexane. Melting point: 149–150° C.

Provenance & Evidence