反应详情

To a solution of 1.08 g (3.38 mmol) di-tert-butyl N-(tert-butoxycarbonyl)-L-glutamate in tetrahydrofuran (18 mL) at −78° C., lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (1.0 M in tetrahydrofuran, 6.20 mL) was added dropwise. The solution was stirred for 2 h, then 1-[3-(benzyloxy)propyl]-4-(bromomethyl)benzene (1.01 g, 2.82 mmol) dissolved in 5 mL tetrahydrofuran were added slowly. The reaction was stirred for additional 2 h and then quenched by the addition of 10 mL of 2 N aqueous hydrogen chloride. The mixture was warmed to room temperature poured into 10 mL 1 N aqueous hydrogen chloride and extracted with dichloromethane (3×30 mL). The organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude product was purified on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

1. additionwere added slowly
2. stirringThe reaction was stirred for additional 2 h
3. customquenched by the addition of 10 mL of 2 N aqueous hydrogen chloride
4. additionpoured into 10 mL 1 N aqueous hydrogen chloride
5. extractionextracted with dichloromethane (3×30 mL)
6. dry with materialThe organic phases were dried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customThe crude product was purified on silica gel using a hexane/ethyl acetate gradient
9. concentrationconcentrated