反应详情

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepane (1.7 g, 5.37 mmol), tetrahydrofuran (45 mL), and dimethylformamide (5 mL). Cool in an ice-bath. Add sodium hydride (0.32 g, 60%n in oil, 8.06 mmol). After 15 minutes, warm to ambient temperature. When gas evolution ceases add 2-(chloromethyl)furan (0.94 g, 8.06 mmol). After 18 hours, cool the reaction mixture, quench by the addition of a saturated aqueous ammonium chloride solution. Evaporate to remove most of the tetrahydrofuran, dilute with ethyl acetate, and extract with water, a saturated aqueous sodium bicarbonate solution, and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 50% ethyl acetate/hexane to give 1-(t-butoxycarbonyl)-4-(fur-2-ylmethyl-1H-benzimidazol-2-yl)[1,4]diazepane: Rf=0.47 (silica gel, ethyl acetate). Elemental Analysis Calculated for C22H28N4O3: C, 66.66; H, 7.17; N, 14.04. Found C, 66.65; H, 7.12; N, 14.13.

1. temperatureCool in an ice-bath
2. waitAfter 18 hours
3. temperaturecool the reaction mixture
4. customquench by the addition of a saturated aqueous ammonium chloride solution
5. customEvaporate
6. customto remove most of the tetrahydrofuran
7. additiondilute with ethyl acetate
8. extractionextract with water
9. dry with materialDry the organic layer over MgSO4
10. filtrationfilter
11. customevaporate in vacuo
12. customto give a residue