Glycolic 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 255807

Reaktionsgleichung

Reaktionsgleichung von HRID 255807
[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].C(O)(=O)[CH2:28][OH:29].S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+]>S(=O)(=O)(O)O.[N+]([O-])([O-])=O.[Ag+]>[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]([CH2:28][OH:29])[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 757Glycolic AcidHCID 24360CamptothecinHCID 62648Ammonium Persulfate

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)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

Camptothecin (50 mg, 0.143 m-mol) was dissolved in 75% sulfuric acid (3 ml). To this solution were added glycolic acid (500 mg, 6.57 m-mol) and silver nitrate (250 mg, 1.31 m-mol) and then was added dropwise under heating (100°-110° C.) and agitation and aqueous solution (15 ml) of ammonium persulfate (3.00 g, 0.0131 m-mol) over 2 hours. After the reaction mixture was allowed to cool, ice water (100 ml) was poured into the reaction mixture which was then extracted with chloroform (100 ml×3). The chloroform layers were combined, washed with a 7% aqueous solution of sodium bicarbonate (300 ml) and then with a saturated edible salt solution (100 ml), dried with anhydrous magnesium sulfate, filtered and evaporated until dryness under reduced pressure. The residue was subjected to thin layer chromatography (5% methanol-chloroform) to effect separation and purification of 7-hydroxymethylcamptothecin whereupon 10.3 mg (19.0%) of pure 7-hydroxymethylcamptothecin were obtained. Besides this, 10.7 mg of camptothecin were recovered.

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureto cool
  3. extractionwas then extracted with chloroform (100 ml×3)
  4. washwashed with a 7% aqueous solution of sodium bicarbonate (300 ml)
  5. dry with materialwith a saturated edible salt solution (100 ml), dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated until dryness under reduced pressure
  8. customseparation and purification of 7-hydroxymethylcamptothecin whereupon 10.3 mg (19.0%) of pure 7-hydroxymethylcamptothecin
  9. customwere obtained
  10. customBesides this, 10.7 mg of camptothecin were recovered

Quellen und Nachweise

ORD-Eintrag
ord-fc5023fe01dc4785a66e34e5a83e4190
Quelldatensatz
uspto-grants-1987_10
Patentnummer
USRE032518

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