Hydrogen Peroxide → 7-Ethylcamptothecin

HRID 255810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 255810
[C:1](O)(=O)[CH2:2]C.[CH3:6][CH2:7][C@@:8]1([OH:31])[C:13](=[O:14])[O:12][CH2:11][C:10]2[C:15]([N:17]3[C:29](=[CH:30][C:9]1=2)[C:28]1[N:27]=[C:26]2[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]2)=[CH:20][C:19]=1[CH2:18]3)=[O:16].S(=O)(=O)(O)O.OO>O>[CH3:1][CH2:2][C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:27]=[C:28]2[C:19]=1[CH2:18][N:17]1[C:15](=[O:16])[C:10]3[CH2:11][O:12][C:13]([C@:8]([OH:31])([CH2:7][CH3:6])[C:9]=3[CH:30]=[C:29]12)=[O:14]

Komponenten

6

Edukt 4

HCID 784Hydrogen Peroxide2×HCID 1032Propionic AcidHCID 1118Sulfuric AcidHCID 24360Camptothecin

Produkt 1

HCID 1275847-Ethylcamptothecin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Ferrous sulfate heptahydrate (1.20 g, 4.31 m-mol) and propionic acid was dissolved in water (15 ml). Camptothecin (300 mg, 0.862 m-mol) was suspended in the solution and dissolved therein by addition of concentrated sulfuric acid (6 ml) in small portions. To this solution was added dropwise under ice-cooling and agitation a 30% aqueous solution of hydrogen peroxide (1 ml, 9.81 m-mol) in small portions over the period of about 10 minutes. After addition of the hydrogen peroxide, the agitation was continued for 16 hours at room temperature. The reaction mixture was diluted with ice water (300 ml) and extracted with chloroform (400 ml). The chloroform layer was dried with magnesium sulfate, filtered and evaporated until dryness under reduced pressure. The residue was subjected to column chromatography (chloroform) through silica gel (10 g) to effect separation and purification of the product whereby 73 mg (22.5 g) of the objective compound were obtained as a yellow white solid.

Aufarbeitung

  1. dissolutiondissolved
  2. additionTo this solution was added dropwise under ice-
  3. temperaturecooling
  4. customover the period of about 10 minutes
  5. extractionextracted with chloroform (400 ml)
  6. dry with materialThe chloroform layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated until dryness under reduced pressure
  9. customseparation and purification of the product whereby 73 mg (22.5 g) of the objective compound
  10. customwere obtained as a yellow white solid

Quellen und Nachweise

ORD-Eintrag
ord-19deb6a7288e41a987b86007ed8e5bd0
Quelldatensatz
uspto-grants-1987_10
Patentnummer
USRE032518

Notizen zur Reaktion

Wird geladen…