Rubitecan → 9-Aminocamptothecin

HRID 1416890

Reaktionsgleichung

Reaktionsgleichung von HRID 1416890
[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]

Komponenten

4

Edukt 1

HCID 472335Rubitecan

Produkt 1

HCID 724029-Aminocamptothecin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2635dc9821c140f5b5f887f656b4a522
Quelldatensatz
uspto-grants-1999_06
Patentnummer
US05916897

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