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 1489136

Reaktionsgleichung

Reaktionsgleichung von HRID 1489136
[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]

Komponenten

6

Edukt 3

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 24360Camptothecin

Produkt 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)-Ausbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b57b34fd6f9a4423a6ba4d8b863cff2f
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677286

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