反应详情

Ethylene glycol dimethyl ether (1.4 mL), water (0.42 mL), phenylboranic acid (0.045 g), sodium bicarbonate (0.063 g), and bis(triphenylphosphine)palladium(II) dichloride (4 mg) were added to tert-butyl 2-(2-acetoxy-5-bromobenzamido)-4-phenylbenzoate (0.15 g), followed by heating to reflux under a nitrogen atmosphere for 45 minutes. The reaction mixture was cooled to room temperature, and potassium carbonate (0.12 g) was added thereto, followed by stirring under a nitrogen atmosphere at room temperature for 2 hours. Water and ethyl acetate were added to the reaction mixture. 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. Methanol (2 mL), dioxane (4 mL), and a 2 mol/L aqueous solution of sodium hydroxide (1.5 mL) were added to the obtained residue, followed by stirring at room temperature for 1 hour and 40 minutes. The solvent was evaporated under reduced pressure, and 1 mol/L hydrochloric acid and ethyl acetate were added to the residue. 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: 95-80% hexane/ethyl acetate] and further purified by silica gel column chromatography [eluent: chloroform] to obtain 0.086 g of tert-butyl 2-(2-hydroxy-5-phenylbenzamido)-4-phenylbenzoate as a white solid.

1. temperatureby heating
2. temperatureto reflux under a nitrogen atmosphere for 45 minutes
3. customThe organic layer was separated
4. washwashed with a saturated aqueous solution of sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. additionMethanol (2 mL), dioxane (4 mL), and a 2 mol/L aqueous solution of sodium hydroxide (1.5 mL) were added to the obtained residue
8. stirringby stirring at room temperature for 1 hour and 40 minutes
9. customThe solvent was evaporated under reduced pressure, and 1 mol/L hydrochloric acid and ethyl acetate
10. additionwere added to the residue
11. customThe organic layer was separated
12. washwashed with a saturated aqueous solution of sodium chloride
13. dry with materialdried over anhydrous magnesium sulfate
14. customthe solvent was evaporated under reduced pressure
15. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 95-80% hexane/ethyl acetate]
16. customfurther purified by silica gel column chromatography [eluent: chloroform]