反应详情

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepane (3.06 g, 9.67 mmol) and sodium hydride (0.43 g, 60% in oil, 10.64 mmol) in tetrahydrofuran (60 mL) and dimethylformamide (6 mL). After 2 hours, add 2-(t-butyldimethylsilyloxy)ethyl iodide (2.78 g, 9.67 mmol). After 20 hours, heat to reflux. After 4 hours, cool to ambient temperature and add ice to quench. Evaporate in vacuo to remove most of the tetrahydrofuran. Partition the evaporated reaction mixture between ethyl acetate (250 mL) and water (200 mL). Separate the layers and extract the organic layer with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give 1-(t-butoxycarbonyl)-4-(1-(2-(t-butyldimethylsilyloxy)ethyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf=0.58 (silica gel, ethyl acetate).

1. waitAfter 20 hours
2. temperatureheat to reflux
3. waitAfter 4 hours
4. additionadd ice
5. customto quench
6. customEvaporate in vacuo
7. customto remove most of the tetrahydrofuran
8. customPartition
9. customthe evaporated reaction mixture between ethyl acetate (250 mL) and water (200 mL)
10. customSeparate the layers
11. extractionextract the organic layer with water
12. dry with materialDry the organic layer over MgSO4
13. filtrationfilter
14. customevaporate in vacuo
15. customto give a residue