反应详情

温度

23 °C

A mixture of 2-((tert-butoxycarbonyl)amino)-6-methylheptanoic acid (3.5 g; 0.0135 mol) and cesium carbonate (4.89 g; 0.015 mol) in 100 ml ethanol was agitated at about 23° C. for about 1 hour. The ethanol was eliminated by evaporation under reduced pressure in a rotative evaporator. The mixture obtained was dissolved in 100 ml of dimethylformamide and 3-bromophenacyl bromide (3.75 g; 0.0135 mol) was then added. After about 16 hours agitation, the solvent was evaporated under reduced pressure. The mixture obtained was taken up in ethyl acetate and the cesium bromide was then filtered. The ethyl acetate of the filtrate was evaporated and the reaction oil was taken up in a mixture of xylene (100 ml) and ammonium acetate (46.2 g; 0.6 mol). The mixture was then heated to reflux for about one hour and a half and, after cooling, a mixture of icy water and ethyl acetate was poured in the reaction medium. After phase separation, the organic phase was washed with a sodium saturated bicarbonate solution, dried over magnesium sulfate and then evaporated under vacuum. The solid obtained was filtered and then washed with ether to produce a white powder (yield of 63%). Melting point: 134-136° C. MH+=436.2.

1. customThe ethanol was eliminated by evaporation under reduced pressure in a rotative evaporator
2. customThe mixture obtained
3. waitAfter about 16 hours agitation
4. customthe solvent was evaporated under reduced pressure
5. customThe mixture obtained
6. filtrationthe cesium bromide was then filtered
7. customThe ethyl acetate of the filtrate was evaporated
8. customthe reaction oil
9. temperatureThe mixture was then heated
10. temperatureto reflux for about one hour
11. temperaturea half and, after cooling
12. additionwas poured in the reaction medium
13. customAfter phase separation
14. washthe organic phase was washed with a sodium saturated bicarbonate solution
15. dry with materialdried over magnesium sulfate
16. customevaporated under vacuum
17. customThe solid obtained
18. filtrationwas filtered
19. washwashed with ether