Citric Acid → HCID 66990857, compound

Participants

Reaction Steps

Piperidine (0.049 mL), cesium carbonate (0.22 g), tris(dibenzylideneacetone)dipalladium(0) (3.0 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (7.9 mg), and palladium(II) acetate (1.5 mg) were added to a toluene (2.0 mL) suspension of tert-butyl 2-(2-(benzyloxy)-4-iodobenzamido)-4-phenylbenzoate (0.20 g), followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and then piperidine (0.033 mL), cesium carbonate (0.11 g), tris(dibenzylideneacetone)dipalladium(0) (3.0 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (7.9 mg), and palladium(II) acetate (1.5 mg) were added thereto, followed by heating to reflux under a nitrogen atmosphere for 4 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-85% hexane/ethyl acetate] to obtain 0.13 g of tert-butyl 2-(2-(benzyloxy)-4-(piperidin-1-yl)benzamido)-4-phenylbenzoate.

Provenance & Evidence