Camptothecin → HCID 11024585, compound

HRID 2418790Notes

Reaction equation

HRID 2418790 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]>C(O)(=O)C.[Pt]=O>[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)[CH:23]1[CH:14]([CH2:15][C:16]2[C:21]([NH:22]1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11]

Participants

4

Reactant 1

HCID 24360Camptothecin

Product 1

HCID 11024585HCID 11024585, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Camptothecin (500 mg, 1.43 m-mol) is suspended in acetic acid (100 ml). Platinum oxide (100 mg) is added to the suspension and the mixture is subjected to catalytic reduction (1.5 hours, absorption of about 140 ml of hydrogen) at room temperature under atmospheric pressure. After removing the catalyst by filtration, the reaction mixture is evaporated until dryness under reduced pressure. The residue is taken up in chloroform (200 ml) and washed with a 5% aqueous solution of sodium hydrogen carbonate (100 ml) and then with a saturated solution of sodium chloride (100 ml). The chloroform phase is dried over magnesium sulfate, filtered and evaporated under reduced pressure until dryness. The residue is purified by column chromatography (chloroform) on silica gel (20 g) whereby 285 mg (conversion rate: 56.3%; yield: 76.7%) of the objective compound is obtained as yellowish white crystals. Unreacted starting materials (113 mg in crude state) is recovered. M.P. (dec.) 240°-242° C. (from methanol)

Workup

  1. customthe mixture is subjected to catalytic reduction (1.5 hours, absorption of about 140 ml of hydrogen) at room temperature under atmospheric pressure
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. customthe reaction mixture is evaporated until dryness under reduced pressure
  5. washwashed with a 5% aqueous solution of sodium hydrogen carbonate (100 ml)
  6. dry with materialThe chloroform phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure until dryness
  9. customThe residue is purified by column chromatography (chloroform) on silica gel (20 g) whereby 285 mg (conversion rate: 56.3%; yield: 76.7%) of the objective compound
  10. customis obtained as yellowish white crystals
  11. customis recovered
  12. customM.P. (dec.) 240°-242° C. (from methanol)

Sources & evidence

ORD record
ord-04b16eec707b46d5a78401edbfc7240a
Source dataset
uspto-grants-1984_09
Patent number
US04473692

Reaction notes

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