反应详情

温度

5 °C

(S)-Benzyl-3-hydroxyglutaramate (100 g) was dissolved in dimethyl formamide. To this Imidazole (35 g) was added and the solution was cooled to 5° C. To this a solution of tert-butyldimethylsilylchloride (68.5 g) dissolved in dimethyl formamide (250 ml) was added under cooling. The mixture was warmed to 20-25° C. and stirred. The reaction mixture was cooled and quenched with water. To the reaction mixture ethyl acetate and water was added and stirred. The layers were separated and the organic phase was washed thrice with water. To the organic phase Palladium on charcoal (5%, 1 g) was added and stirred under hydrogen atmosphere (˜2.8 Kg). Palladium was removed by filtration. The filtrate was mixed with water and adjusted pH to ˜9.0 by using Aq ammonia solution. The reaction mass was stirred and layers were separated. The aqueous phase was washed with dichloromethane and dichloromethane was added to aqueous phase. The reaction mass was cooled to 5° C. and pH was adjusted to 4.0 with Aq phosphoric acid. The reaction mass was stirred and layers were separated. The organic phase was washed with water and dried over sodium sulphate. The organic layer was evaporated under vacuum to yield residue. Residue was dissolved in dichloromethane and to this solution heptane was added, stirred, filtered and dried to yield (S)-3-(tert-butyl dimethylsilyloxy)glutaric acid monoamide.

1. additionwas added
2. temperatureunder cooling
3. temperatureThe mixture was warmed to 20-25° C.
4. temperatureThe reaction mixture was cooled
5. customquenched with water
6. additionTo the reaction mixture ethyl acetate and water was added
7. stirringstirred
8. customThe layers were separated
9. washthe organic phase was washed thrice with water
10. additionTo the organic phase Palladium on charcoal (5%, 1 g) was added
11. stirringstirred under hydrogen atmosphere (˜2.8 Kg)
12. customPalladium was removed by filtration
13. additionThe filtrate was mixed with water and adjusted pH to ˜9.0
14. stirringThe reaction mass was stirred
15. customlayers were separated
16. washThe aqueous phase was washed with dichloromethane and dichloromethane
17. additionwas added to aqueous phase
18. temperatureThe reaction mass was cooled to 5° C.
19. stirringThe reaction mass was stirred
20. customlayers were separated
21. washThe organic phase was washed with water
22. dry with materialdried over sodium sulphate
23. customThe organic layer was evaporated under vacuum
24. customto yield residue
25. additionwas added
26. stirringstirred
27. filtrationfiltered
28. customdried