反应详情

1-(tert-Butoxycarbonyl)-4-hydroxypiperidine (0.047 g), cesium carbonate (0.075 g), 1,10-phenanthroline (4.2 mg), and copper(I) iodide (2.2 mg) were added to a toluene (1 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-iodobenzamido)-4-phenylbenzoate (0.070 g), followed by heating to reflux under a nitrogen atmosphere for 4 hours. The reaction mixture was cooled to room temperature, and then 1-(tert-butoxycarbonyl)-4-hydroxypiperidine (0.047 g), cesium carbonate (0.075 g), 1,10-phenanthroline (4.2 mg), and copper(I) iodide (2.2 mg) were added to the reaction mixture, followed by heating to reflux under a nitrogen atmosphere for 2 hours. The reaction mixture was cooled to room temperature, and then 1,10-phenanthroline (4.2 mg) and copper(I) iodide (2.2 mg) were added to the reaction mixture, followed by heating to reflux under a nitrogen atmosphere for 5 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: 95-60% hexane/ethyl acetate] to obtain 0.074 g of tert-butyl 4-(2-(2-(benzyloxy)-5-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)benzamido)-4-phenylbenzoyloxy)piperidine-1-carboxylate.

1. temperatureby heating
2. temperatureto reflux under a nitrogen atmosphere for 4 hours
3. temperatureby heating
4. temperatureto reflux under a nitrogen atmosphere for 2 hours
5. temperatureThe reaction mixture was cooled to room temperature
6. temperatureby heating
7. temperatureto reflux under a nitrogen atmosphere for 5 hours and 30 minutes
8. temperatureThe reaction mixture was cooled to room temperature
9. customThe insoluble substance was removed by filtration
10. customThe organic layer was separated
11. washwashed with a saturated aqueous solution of sodium chloride
12. dry with materialdried over anhydrous magnesium sulfate
13. customthe solvent was evaporated under reduced pressure
14. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 95-60% hexane/ethyl acetate]