1-Butanol → 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-11-propyl-, (S)-

HRID 255811

Reaction equation

HRID 255811 reaction equation
[CH2:1](O)[CH2:2][CH2:3]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][CH2:3][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 2631-ButanolHCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 24360Camptothecin

Product 1

HCID 1496121H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-11-propyl-, (S)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ferrous sulfate heptahydrate (2.8 g, 10.1 m-mol) and 1-butanol (3 ml, 43 m-mol) were dissolved in water (30 ml). Camptothecin (500 mg, 1.43 m-mol) was suspended in the solution and dissolved therein by addition of concentrated sulfuric acid (15 ml). To this solution was added dropwise under ice-cooling and agitation a 30% aqueous solution of hydrogen peroxide (1.1 ml, 10.1 m-mol) in small portions. The agitation was continued for 4 hours at room temperature. The reaction mixture was diluted with ice water (1.5 l) and extracted with chloroform (2 l). 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 (15 g) to effect separation and purification of the product which was then recrystallized from n-hexane-chloroform whereby 110 mg (21.0%) of the objective compound were obtained as light yellow white needle crystals. M.P. 260°-261° C.

Workup

  1. dissolutiondissolved
  2. additionTo this solution was added dropwise under ice-
  3. temperaturecooling
  4. extractionextracted with chloroform (2 l)
  5. dry with materialThe chloroform layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated until dryness under reduced pressure
  8. customseparation and purification of the product which
  9. customwas then recrystallized from n-hexane-chloroform whereby 110 mg (21.0%) of the objective compound
  10. customwere obtained as light yellow white needle crystals

Sources & evidence

ORD record
ord-79a77d71353d483fafa1842e7a6b9e16
Source dataset
uspto-grants-1987_10
Patent number
USRE032518

Linked notes

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