Rubitecan → 9-Aminocamptothecin

HRID 977512

Reaktionsgleichung

Reaktionsgleichung von HRID 977512
[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-f05c10cd58c640e2a1f61d489d7f6032
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614628

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