Reaktion #417938

Reaktionsgleichung

epirubicin hydrochloride

diisopropyl ethyl amine

water

4-chlorobutyryl chloride

→

object product

Ausbeute 64.0%

epirubicin

Ausbeute 64.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to 0° C.-5° C. in an ice bath
2. 2
   workup.WAITThe reaction was performed for 30 min
3. 3
   ExtraktionThe resulting mixture was extracted with chloroform three times (5 ml×3)
4. 4
   WaschenThe combined layers were washed once with saline
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigerotary-evaporated
8. 8
   Sonstigeto remove the solvent
9. 9
   SonstigeThe resultant product was purified with thin layer chromatography
10. 10
    Wascheneluted with chloroform
11. 11
    workup.DISSOLUTIONmethanol=95:5.8 mg of the product were dissolved in 3 ml of anhydrous DMF
12. 12
    Temperaturcooled 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
    ExtraktionThe resultant mixture was extracted three times with chloroform (5 ml×3)
17. 17
    WaschenThe combined layers were washed once with saturated saline
18. 18
    Trocknendried over anhydrous magnesium sulfate
19. 19
    Filtrationfiltered
20. 20
    Sonstigerotary-evaporated
21. 21
    Sonstigeto remove the solvent
22. 22
    SonstigeThe product was purified with thin layer chromatography
23. 23
    Wascheneluted with chloroform

Vorschrift

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

Quelle