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

HRID 1584630

반응식

HRID 1584630 반응식
[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].OO.[CH3:29][OH:30]>O.OS(O)(=O)=O>[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]([CH2:29][OH:30])[C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11]

참가 물질

6

반응물 3

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 24360Camptothecin

생성물 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)-수율 99%

시약·촉매·용매 2

HCID 962Water용매HCID 1118Sulfuric Acid용매

반응 조건

온도
0 °C

실험 절차

Camptothecin (20.0 g) was dissolved in mixture of methanol (750 mL), water (500 mL), conc. H2SO4 (500 mL) and finely ground FeSO4 (16.0 g) and hydrogen peroxide (100 mL 30% solution) was added dropwise over the course of 2 h and the reaction mixture was allowed to stir for another hour. The reaction mixture was then filtered through a sintered glass funnel to remove all undissolved material. The resultant filtrate was then cooled to 0° C. and NaOH (375 g) in 1 L water was added slowly with vigorous stirring. The yellow-brown solid was then filtered, washed with water and pumped to dryness. The resultant crude product was then placed in a 1 L erlenmyer flask, DMF (300 mL) added and warmed to 110° C. Once the solid is dispersed into small particles, acetonitrile (500 mL) was added and the mixture heated until boiling. The mixture was then allowed to cool to room temperature then 0° C., filtered and the solid washed with chloroform to provide 7-hydroxymethylcamptothecin (21.50 g, 99%) as a pale yellow solid.

후처리

  1. additionwas added dropwise over the course of 2 h
  2. filtrationThe reaction mixture was then filtered through a sintered glass funnel
  3. customto remove all undissolved material
  4. additionNaOH (375 g) in 1 L water was added slowly with vigorous stirring
  5. filtrationThe yellow-brown solid was then filtered
  6. washwashed with water
  7. customThe resultant crude product was then placed in a 1 L erlenmyer flask
  8. additionDMF (300 mL) added
  9. temperaturewarmed to 110° C
  10. additionOnce the solid is dispersed into small particles, acetonitrile (500 mL)
  11. additionwas added
  12. temperaturethe mixture heated until boiling
  13. temperatureto cool to room temperature
  14. filtration0° C., filtered
  15. washthe solid washed with chloroform

출처 및 근거

ORD 기록
ord-feb5bffbfa0f4b5daa870f1aee977f59
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05932709

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