反应 #417938

反应方程式

epirubicin hydrochloride

diisopropyl ethyl amine

water

4-chlorobutyryl chloride

→

object product

收率 64.0%

epirubicin

收率 64.0%

溶剂

DMF

反应条件

后处理

1. 1
   温度The mixture was cooled to 0° C.-5° C. in an ice bath
2. 2
   workup.WAITThe reaction was performed for 30 min
3. 3
   萃取The resulting mixture was extracted with chloroform three times (5 ml×3)
4. 4
   洗涤The combined layers were washed once with saline
5. 5
   干燥dried over anhydrous magnesium sulfate
6. 6
   过滤filtered
7. 7
   其他rotary-evaporated
8. 8
   其他to remove the solvent
9. 9
   其他The resultant product was purified with thin layer chromatography
10. 10
    洗涤eluted with chloroform
11. 11
    workup.DISSOLUTIONmethanol=95:5.8 mg of the product were dissolved in 3 ml of anhydrous DMF
12. 12
    温度cooled 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
    萃取The resultant mixture was extracted three times with chloroform (5 ml×3)
17. 17
    洗涤The combined layers were washed once with saturated saline
18. 18
    干燥dried over anhydrous magnesium sulfate
19. 19
    过滤filtered
20. 20
    其他rotary-evaporated
21. 21
    其他to remove the solvent
22. 22
    其他The product was purified with thin layer chromatography
23. 23
    洗涤eluted with chloroform

实验过程

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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