反应详情

In 90 ml of N,N-dimethylformamide was dissolved 9.0 g of methyl 4-(1-carboxycyclopropyl)-2,3,5,6-tetrafluorobenzoate. To the resulting solution were added, with ice-cooling, 4.0 g of ethyl chlorocarbonate and 3.7 g of triethylamine in this order. The resulting mixture was stirred at the same temperature for 30 minutes. Then, 2.6 g of sodium azide was added thereto with ice-cooling. The resulting mixture was stirred at the same temperature for 1 hour. To the reaction mixture were added 150 ml of ethyl acetate and 300 ml of water in this order. The resulting mixture was adjusted to pH 1 with 2N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in a mixture of 90 ml of dioxane and 8.1 g of benzyl alcohol. The resulting solution was refluxed for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene) to obtain 10.6 g (yield: 86.9%) of methyl 4-(1-benzyloxycarbonylaminocyclopropyl)-2,3,5,6-tetrafluorobenzoate.

1. additionTo the resulting solution were added, with ice-
2. temperaturecooling
3. temperaturewith ice-cooling
4. stirringThe resulting mixture was stirred at the same temperature for 1 hour
5. customThe organic layer was separated
6. washwashed with water
7. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
8. customThe solvent was removed by distillation under reduced pressure
9. customThe residue obtained
10. temperatureThe resulting solution was refluxed for 1 hour
11. concentrationThe reaction mixture was concentrated under reduced pressure
12. customThe residue obtained
13. customwas purified by a column chromatography (eluant: toluene)