Hydrogen Peroxide → 7-Ethylcamptothecin

HRID 255810

반응식

HRID 255810 반응식
[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]

참가 물질

6

반응물 4

HCID 784Hydrogen Peroxide2회HCID 1032Propionic AcidHCID 1118Sulfuric AcidHCID 24360Camptothecin

생성물 1

HCID 1275847-Ethylcamptothecin

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-19deb6a7288e41a987b86007ed8e5bd0
출처 데이터셋
uspto-grants-1987_10
특허 번호
USRE032518

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