Aniline → 7-Phenyliminomethylcamptothecin

HRID 1356983

Reaktionsgleichung

Reaktionsgleichung von HRID 1356983
[CH3:1][CH2:2][C@@:3]1([OH:28])[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[C:14](=[C:15]([CH:26]=O)[C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11].[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[Yb]>C(Cl)Cl>[CH3:1][CH2:2][C@@:3]1([OH:28])[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[C:14](=[C:15]([CH:26]=[N:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]3)=[O:11]

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 23992YtterbiumHCID 1498761H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-11-carboxaldehyde, 4-ethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-, (S)-

Produkt 1

HCID 98684337-PhenyliminomethylcamptothecinAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

100 mg (0.26 mmoles) of 7-formylcamptothecin, dissolved into 20 ml of methylene chloride, and 25 μl (0.26 mmoles) of aniline, dissolved into 0.5 ml of methylene chloride, were added to a suspension of ytterbium triphlate (16.5 mg. 0.026 mmoles, 10 % mol) in 5 ml of methylene chloride containing MS 4A and were left 3.5 hours under stirring at room T, then the solvent was evaporated under vacuum. The product was purified by means of flash chromatography on silica gel using a mixture of methylene chloride/methanol 98/2 as eluant. 60 mg of a yellow solid were obtained.

Aufarbeitung

  1. customthe solvent was evaporated under vacuum
  2. customThe product was purified by means of flash chromatography on silica gel using
  3. additiona mixture of methylene chloride/methanol 98/2 as eluant

Quellen und Nachweise

ORD-Eintrag
ord-ceca403a786e4758ad8483023a9ba01a
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06589939B2

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