Trifluoroacetic acid → 3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid diisobutylamide
Reaktionsgleichung
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19](=[O:29])[N:20]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:17]=2)[NH:12][C:11]=1[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH2:21]([N:20]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:19]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:30]1[CH:31]=[C:32]([CH3:37])[CH:33]=[C:34]([CH3:36])[CH:35]=1)=[C:10]2[CH2:9][CH2:8][NH2:7])=[O:29])[CH:22]([CH3:24])[CH3:23]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of {2-[5-diisobutylcarbamoyl-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethyl}carbamic acid tert-butyl ester (230 mg in 12 mL methylene chloride) at 0° C. was added 0.55 mL anisole followed by 3.4 mL trifluoroacetic acid and the mixture stirred at 0° C. After 1 hour, the mixture was concentrated in vacuo and the residual acid removed by azeotrope with toluene. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:8:1) gave the title compound (173 mg).
Aufarbeitung
- concentrationthe mixture was concentrated in vacuo
- customthe residual acid removed by azeotrope with toluene
- customPurification of the
- concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 90:8:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-ec8c489db6cc43499785403e7eea2246
- Quelldatensatz
- uspto-grants-2000_12
- Patentnummer
- US06156767
Notizen zur Reaktion
Wird geladen…