反应详情

To a solution of ethyl 2-t-butoxycarbonylamino-3-nitrobenzoate (20 g) in tetrahydrofuran (50 ml) was added, while stirring under ice-cooling, sodium hydride (60% dispersion in mineral oil, 2.8 g). The mixture was stirred at room temperature for 20 minutes and to the mixture were then added 4-(2-cyanophenyl)benzyl bromide (18 g) and potassium iodide (360 mg), followed by heating for 10 hours under reflux. The solvent was evaporated to dryness and the residue was partitioned between water (250 ml) and ether (200 ml). The organic layer was washed with water, dried and concentrated to give a yellow syrup. The syrup was dissolved in a mixture of trifluoroacetic acid (60 ml) and methylene chloride (40 ml) and the solution was stirred for one hour at room temperature. The reaction mixture was concentrated to dryness and to the residue was added ethyl ether (200 ml) to give crystals. The crystals were collected by filtration, washed with ether to give pale yellow crystals (22.1 g, 85%), m.p. 118°-119° C.

1. temperaturecooling
2. stirringThe mixture was stirred at room temperature for 20 minutes and to the mixture
3. temperatureby heating for 10 hours
4. temperatureunder reflux
5. customThe solvent was evaporated to dryness
6. customthe residue was partitioned between water (250 ml) and ether (200 ml)
7. washThe organic layer was washed with water
8. customdried
9. concentrationconcentrated
10. customto give a yellow syrup
11. stirringthe solution was stirred for one hour at room temperature
12. concentrationThe reaction mixture was concentrated to dryness and to the residue
13. additionwas added ethyl ether (200 ml)
14. customto give crystals
15. filtrationThe crystals were collected by filtration
16. washwashed with ether