Rubitecan → 9-Aminocamptothecin

HRID 977512

Reaction equation

HRID 977512 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-f05c10cd58c640e2a1f61d489d7f6032
Source dataset
uspto-grants-1997_03
Patent number
US05614628

Linked notes

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