反应详情

温度

-78 °C

Di-tert-butyl N-trityl-L-glutamate (1.63 g, 3.25 mmol) was dissolved in tetrahydrofuran (12 ml) and the solution was cooled to −78° C. To the solution was added lithium 1,1,1,3,3,3-hexamethyldisilazide (1M in tetrahydrofuran, 7.14 ml) and, after stirring at −78° C. for 20 min, benzyl 4-(bromomethyl)phenyl ether (1.08 g, 3.90 mmol) in tetrahydrofuran (8 ml) was slowly added. The cooling bath was removed and the reaction mixture was stirred for 2 h. Then, 50 ml of 2 M aqueous hydrogen chloride solution were added and the mixture was extracted with dichloromethane. The organic phase was dried and concentrated under reduced pressure; the residue was purified by silica gel column chromatography to yield 813 mg (30%) of the product.

1. customThe cooling bath was removed
2. stirringthe reaction mixture was stirred for 2 h
3. additionThen, 50 ml of 2 M aqueous hydrogen chloride solution were added
4. extractionthe mixture was extracted with dichloromethane
5. customThe organic phase was dried
6. concentrationconcentrated under reduced pressure
7. customthe residue was purified by silica gel column chromatography