反应 #521983

反应方程式

Camptothecin

sulfuric acid

methanol chloroform

ammonium persulfate

→

7-hydroxymethylcamptothecin

溶剂

methanol

反应条件

后处理

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   workup.ADDITIONby addition under ice-
3. 3
   workup.ADDITIONTo the solution was added dropwise
4. 4
   温度under reflux
5. 5
   萃取the organic matter was extracted with a mixture (1:1, 500 ml) of dioxane-chloroform
6. 6
   干燥dried with anhydrous magnesium sulfate
7. 7
   过滤filtered
8. 8
   其他evaporated until dryness under reduced pressure
9. 9
   温度was warmed (50°-60° C.) with methanol (200 ml)
10. 10
    过滤An insoluble matter was collected by filtration
11. 11
    其他dried under reduced pressure
12. 12
    其他recrystallized from dimethylformamide-dioxane whereupon 40 mg (36.9%) of 7-hydroxymethylcamptothecin
13. 13
    其他were obtained as light yellow white prismatic crystals

实验过程

Camptothecin (100 mg, 0.287 m-mol) was suspended in methanol (25 ml) and then dissolved therein by addition under ice-cooling of 75% sulfuric acid (10 ml). To the solution was added dropwise under reflux with stirring an aqueous solution (100 ml) of ammonium persulfate (15 g, 0.0657 mol) over 16 hours. The reaction mixture was poured into ice water (100 ml) and the organic matter was extracted with a mixture (1:1, 500 ml) of dioxane-chloroform and then thrice with chloroform (100 ml×3). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and then evaporated until dryness under reduced pressure. The remaining solid having an orange color was warmed (50°-60° C.) with methanol (200 ml) and stirred for 30 minutes. An insoluble matter was collected by filtration, dried under reduced pressure and recrystallized from dimethylformamide-dioxane whereupon 40 mg (36.9%) of 7-hydroxymethylcamptothecin were obtained as light yellow white prismatic crystals having a melting point of 274°-276° C. (dec.). Rf value 0.125 (5% methanol-chloroform).

来源