反应详情

tert-Butyl [2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)prop-2-en-1-yl]carbamate (I-325) (97.0 mg, 0.226 mmol) and allyl bromide (28.7 μl, 0.339 mmol) were dissolved in dimethylformamide (2 ml), then with cooling with ice, sodium hydride (55% w/w) (11.8 mg, 0.271 mmol) was added, followed by stirring for 2 hours with cooling with ice. With cooling with ice, aqueous 10% citric acid solution was added to the reaction liquid, followed by concentration under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1, v/v) to obtain the entitled compound (105 mg, 99%) as a colorless oily substance.

1. additionwas added
2. temperaturewith cooling with ice
3. additionwas added to the reaction liquid
4. concentrationfollowed by concentration under reduced pressure
5. dissolutionThe resulting residue was dissolved in ethyl acetate
6. washwashed with water and saturated brine
7. dry with materialAfter drying over anhydrous sodium sulfate
8. customthe insoluble matter was separated by filtration
9. customthe residue obtained by concentration
10. customwas purified by silica gel column chromatography (eluent, n-hexane