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Sulfuric Acid → 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-11-(hydroxymethyl)-, (S)-

HRID 255805
ノート
印刷プレビュー

反応式

HRID 255805 の反応式
[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11].S(=O)(=O)(O)O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[CH3:44][OH:45].C(Cl)(Cl)Cl>CO>[CH3:1][CH2:2][C@@:3]1([OH:26])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[C:14](=[C:15]([CH2:44][OH:45])[C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 24360CamptothecinHCID 62648Ammonium PersulfateHCID 21584188Chloroform methanol

生成物 1

HCID 1496101H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-11-(hydroxymethyl)-, (S)-

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

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).

後処理

  1. dissolutiondissolved
  2. additionby addition under ice-
  3. additionTo the solution was added dropwise
  4. temperatureunder reflux
  5. extractionthe organic matter was extracted with a mixture (1:1, 500 ml) of dioxane-chloroform
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated until dryness under reduced pressure
  9. temperaturewas warmed (50°-60° C.) with methanol (200 ml)
  10. filtrationAn insoluble matter was collected by filtration
  11. customdried under reduced pressure
  12. customrecrystallized from dimethylformamide-dioxane whereupon 40 mg (36.9%) of 7-hydroxymethylcamptothecin
  13. customwere obtained as light yellow white prismatic crystals

出典と根拠

ORDレコード
ord-02d98f1c2f7c48a680b8802981bcbaa0
出典データセット
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
USRE032518

反応ノート

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