Hydrogen Peroxide → 7-Ethylcamptothecin

HRID 255810

Reaction equation

HRID 255810 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 1275847-Ethylcamptothecin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-19deb6a7288e41a987b86007ed8e5bd0
Source dataset
uspto-grants-1987_10
Patent number
USRE032518

Linked notes

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