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

반응식

HRID 255806 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].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]

참가 물질

6

반응물 5

HCID 784Hydrogen Peroxide2회HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 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)-

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-da13503ef0124e3c9c956f411bd8568f
출처 데이터셋
uspto-grants-1987_10
특허 번호
USRE032518

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