Hydrogen Peroxide → 7-Ethylcamptothecin

HRID 255809

Reaction equation

HRID 255809 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].[CH2:27](O)[CH2:28]C.OO>S(=O)(=O)(O)O>[CH3:27][CH2:28][C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:22]=[C:23]2[C:14]=1[CH2:13][N:12]1[C:10](=[O:11])[C:5]3[CH2:6][O:7][C:8]([C@:3]([OH:26])([CH2:2][CH3:1])[C:4]=3[CH:25]=[C:24]12)=[O:9]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 10311-PropanolHCID 24360Camptothecin

Product 1

HCID 1275847-Ethylcamptothecin

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In an aqueous solution of sulfuric acid (15 ml of concentrated sulfuric acid in 30 ml of water) were dissolved camptothecin (1.00 g, 2.87 m-mol), ferrous sulfate heptahydrate (5.60 g, 20.1 m-mol) and 1-propanol (6 ml, 86.1 m-mol). To this solution was added dropwise under ice-cooling and agitation a 30% aqueous solution of hydrogen peroxide (2.1 ml, 20.1 m-mol) in small portions. After addition of the hydrogen peroxide, the agitation was continued for one hour at room temperature. The reaction was diluted with ice water (2 l) and extracted with chloroform (2.5 l). The chloroform layer was dried with anhydrous magnesium sulfate, filtered and evaporated until dryness under reduced pressure. The residue was subjected to column chromatography (chloroform) through silica gel (15 g) to effect separation and purification of the product which was then recrystallized from n-hexane-chloroform whereby 265 mg (25.3%) of the objective compound were obtained as light yellow white needle crystals. M.P. 258°-261° C.

Workup

  1. additionTo this solution was added dropwise under ice-
  2. temperaturecooling
  3. extractionextracted with chloroform (2.5 l)
  4. dry with materialThe chloroform layer was dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated until dryness under reduced pressure
  7. customseparation and purification of the product which
  8. customwas then recrystallized from n-hexane-chloroform whereby 265 mg (25.3%) of the objective compound
  9. customwere obtained as light yellow white needle crystals

Sources & evidence

ORD record
ord-db9abdb118064f2393a9387aca86c348
Source dataset
uspto-grants-1987_10
Patent number
USRE032518

Linked notes

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