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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 255806
Notes
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Reaction equation

HRID 255806 reaction equation
[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.[OH2:32].OO.[CH3:35]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]([CH2:35][OH:32])[C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 784Hydrogen Peroxide2×HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 24360Camptothecin

Product 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)-

Procedure

Camptothecin (3.00 g, 8.61 m-mol) was suspended in methanol (90 ml) and then dissolved therein by addition of 75% sulfuric acid (75 ml) and 75 ml of water. To the solution was added FeSO4. 7H2O (40 g, 0.143 mol) and then was added dropwise under ice-cooling and agitation 30% hydrogen peroxide (15 ml) over 2 hours. After addition of the hydrogen peroxide, the reaction mixture was stirred for 14 hours at room temperature and poured into ice water (1 l). The yellowish brown solid precipitated was collected by filtration and dried under reduced pressure whereby 2.5 g of 7-hydroxymethylcamptothecin were obtained. The filtrate was extracted with chloroform (250 ml×4) thereby obtaining 200 mg of crude crystals of the product. 2.7 Grams (82.9%) in toto of 7-hydroxymethylcamptothecin were obtained, which was identified to be the same product as obtained in Example 1 by way of IR-absorption spectra and thin layer chromatography.

Workup

  1. dissolutiondissolved
  2. addition7H2O (40 g, 0.143 mol) and then was added dropwise under ice-
  3. temperaturecooling
  4. customThe yellowish brown solid precipitated
  5. filtrationwas collected by filtration
  6. dry with materialdried under reduced pressure whereby 2.5 g of 7-hydroxymethylcamptothecin
  7. customwere obtained
  8. extractionThe filtrate was extracted with chloroform (250 ml×4)
  9. customthereby obtaining 200 mg of crude crystals of the product

Sources & evidence

ORD record
ord-da13503ef0124e3c9c956f411bd8568f
Source dataset
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE032518

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes