反応 #417938

反応方程式

epirubicin hydrochloride

diisopropyl ethyl amine

water

4-chlorobutyryl chloride

→

object product

収率 64.0%

epirubicin

収率 64.0%

溶媒

DMF

反応条件

後処理

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
   抽出The resulting mixture was extracted with chloroform three times (5 ml×3)
4. 4
   洗浄The combined layers were washed once with saline
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   ろ過filtered
7. 7
   その他rotary-evaporated
8. 8
   その他to remove the solvent
9. 9
   その他The resultant product was purified with thin layer chromatography
10. 10
    洗浄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
    抽出The resultant mixture was extracted three times with chloroform (5 ml×3)
17. 17
    洗浄The combined layers were washed once with saturated saline
18. 18
    乾燥dried over anhydrous magnesium sulfate
19. 19
    ろ過filtered
20. 20
    その他rotary-evaporated
21. 21
    その他to remove the solvent
22. 22
    その他The product was purified with thin layer chromatography
23. 23
    洗浄eluted with chloroform

実験手順

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

出典