9-Methoxycamptothecin → HCID 178438219, compound

HRID 351984Notes

Reaction equation

HRID 351984 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:28])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[C:23]([O:26]C)=[CH:22][CH:21]=[CH:20]2)=[O:11]>Br>[CH3:1][CH2:2][C@@:3]1([OH:28])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[NH:18][C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[C:23](=[O:26])[CH:22]=[CH:21][CH:20]=2)=[O:11]

Participants

3

Reactant 1

HCID 1236179-Methoxycamptothecin

Product 1

HCID 178438219HCID 178438219, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

9-Methoxycamptothecin (9-MC; 10.0 g, 26.43 mmol) was suspended in 47% hydrobromic acid (200 ml), degassed by suction and then displaced by argon gas, and refluxed for 3.5 hr. The reaction mixture was cooled to ambient temperature and poured into water (900 ml) in portion wise under stirring. The deposit was collected on a celite pad and washed with water. The obtained material by filtration was dissolved in chloroform containing 20% methanol, added with active carbon (20 g) and anhydrous sodium sulfate, stirred for 1 hr, filtered, concentrated to dryness under reduced pressure to give a crude product. The crude product was purified through silica gel column chromatography (chloroform containing 8% methanol) to give 9-hydroxycamptothecin (9-HC) as a brown solid; mp 231-237° C. (decomposition) (6.47 g, yield 67%).

Workup

  1. customdegassed by suction
  2. temperaturerefluxed for 3.5 hr
  3. additionpoured into water (900 ml) in portion wise
  4. customThe deposit was collected on a celite pad
  5. washwashed with water
  6. filtrationThe obtained material by filtration
  7. dissolutionwas dissolved in chloroform containing 20% methanol
  8. additionadded with active carbon (20 g) and anhydrous sodium sulfate
  9. stirringstirred for 1 hr
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure
  12. customto give a crude product
  13. customThe crude product was purified through silica gel column chromatography (chloroform containing 8% methanol)

Sources & evidence

ORD record
ord-29789c7e5bcf40d3ac74012437b2de3e
Source dataset
uspto-grants-2004_06
Patent number
US06743918B2

Reaction notes

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