Rubitecan → 9-Aminocamptothecin

HRID 1416890Notes

Reaction equation

HRID 1416890 reaction equation
[CH3:1][CH2:2][C@@:3]1([OH:29])[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]([N+:26]([O-])=O)=[CH:22][CH:21]=[CH:20]2)=[O:11]>CN(C=O)C.[Pd]>[CH3:1][CH2:2][C@@:3]1([OH:29])[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]([NH2:26])=[CH:22][CH:21]=[CH:20]2)=[O:11]

Participants

4

Reactant 1

HCID 472335Rubitecan

Product 1

HCID 724029-Aminocamptothecin

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.6 g of 9-nitro-20(S)-camptothecin in 7.5 ml of DMF was hydrogenated at room temperature and atmospheric pressure in the presence of 0.02 g of 10% Pd/C for four hours. The catalyst was filtered off, and washed with warm DMF repeatedly. The solution was evaporated in vacuo and the crude reaction mixture was purified by column chromatography, to yield the title product.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with warm DMF repeatedly
  4. customThe solution was evaporated in vacuo
  5. customthe crude reaction mixture
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-2635dc9821c140f5b5f887f656b4a522
Source dataset
uspto-grants-1999_06
Patent number
US05916897

Reaction notes

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