Sodium Carbonate → (4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-methoxy-1,1'-biphenyl-4-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

After a 2M aqueous sodium carbonate solution (0.5 ml), tris(dibenzylideneacetone)dipalladium (0) (18 mg, 0.02 mmol) and bis(2-diphenylphosphinophenyl)ether (DPEphos) (22 mg, 0.04 mmol) were added to a solution of tert-butyl 2-hydroxy-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoate (100 mg, 0.20 mmol) obtained in Example (22-4) and methyl (3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate (79 mg, 0.24 mmol) obtained in Example (22-5) in a mixture of toluene-ethanol (6:1, 3.5 ml), the mixture was stirred at 100° C. for 5 hours. After the temperature of the reaction mixture was returned to room temperature, the mixture was poured into water and extracted with ethyl acetate (three times). The organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The compound obtained by removing the solvent under reduced pressure was treated according to a method similar to Example (17-4) to give the title compound as a pale yellow powder (43 mg, yield: 40%).

Provenance & Evidence