반응 #417938

반응 방정식

epirubicin hydrochloride

diisopropyl ethyl amine

water

4-chlorobutyryl chloride

→

object product

수율 64.0%

epirubicin

수율 64.0%

용매

DMF

반응 조건

후처리

1. 1
   온도The mixture was cooled to 0° C.-5° C. in an ice bath
2. 2
   workup.WAITThe reaction was performed for 30 min
3. 3
   추출The resulting mixture was extracted with chloroform three times (5 ml×3)
4. 4
   세척The combined layers were washed once with saline
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   여과filtered
7. 7
   기타rotary-evaporated
8. 8
   기타to remove the solvent
9. 9
   기타The resultant product was purified with thin layer chromatography
10. 10
    세척eluted with chloroform
11. 11
    workup.DISSOLUTIONmethanol=95:5.8 mg of the product were dissolved in 3 ml of anhydrous DMF
12. 12
    온도cooled in an ice bath to a temperature of −5° C. to 0° C
13. 13
    workup.ADDITION0.3 mg of sodium hydride was added to the mixture
14. 14
    workup.STIRRINGThe resulting mixture was stirred for 24 hr
15. 15
    workup.ADDITION50 ml of water were added
16. 16
    추출The resultant mixture was extracted three times with chloroform (5 ml×3)
17. 17
    세척The combined layers were washed once with saturated saline
18. 18
    건조dried over anhydrous magnesium sulfate
19. 19
    여과filtered
20. 20
    기타rotary-evaporated
21. 21
    기타to remove the solvent
22. 22
    기타The product was purified with thin layer chromatography
23. 23
    세척eluted with chloroform

실험 절차

10 mg of epirubicin hydrochloride was dissolved in 5 ml of anhydrous DMF. The mixture was cooled to 0° C.-5° C. in an ice bath. 7 mg of diisopropyl ethyl amine was added to the mixture. The resulting mixture was stirred for 10 min. 2.4 mg of 4-chlorobutyryl chloride was added to the resulting mixture. The reaction was performed for 30 min. 100 ml of water was added to the resultant mixture in an ice bath. The resulting mixture was extracted with chloroform three times (5 ml×3). The chloroform layers were combined. The combined layers were washed once with saline, dried over anhydrous magnesium sulfate, filtered and rotary-evaporated to remove the solvent. The resultant product was purified with thin layer chromatography and eluted with chloroform:methanol=95:5.8 mg of the product were dissolved in 3 ml of anhydrous DMF. The resulting mixture was protected with argon and cooled in an ice bath to a temperature of −5° C. to 0° C. 0.3 mg of sodium hydride was added to the mixture. The resulting mixture was stirred for 24 hr. After the reaction completed, 50 ml of water were added. The resultant mixture was extracted three times with chloroform (5 ml×3). The chloroform layers were combined. The combined layers were washed once with saturated saline, dried over anhydrous magnesium sulfate, filtered and rotary-evaporated to remove the solvent. The product was purified with thin layer chromatography and eluted with chloroform:methanol=30:1 to give 6 mg of the object product. MS: 611

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