Water → N-(2-nitrophenyl)-(2-cyanophenyl)alanine dihexylamide

HRID 651584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 651584
[CH2:1]([N:7]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:8](=[O:20])[C@H:9]([CH3:19])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]#[N:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].F[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N+:34]([O-:36])=[O:35].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:21]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8](=[O:20])[C@H:9]([CH3:19])[N:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]#[N:18])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N+:34]([O-:36])=[O:35])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 54368029(2-Cyanophenyl)alanine dihexylamide

Produkt 1

HCID 54546355N-(2-nitrophenyl)-(2-cyanophenyl)alanine dihexylamideAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The crude (2-cyanophenyl)alanine dihexylamide (0.76 g), 2-fluoronitrobenzene (0.30 g) and anhydrous potassium carbonate (0.36 g) in 8 ml of N,N-dimethylformamide were refluxed under heating for 2.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane-ethyl acetate=5:1) to give 0.42 g of N-(2-nitrophenyl)-(2-cyanophenyl)alanine dihexylamide.

Aufarbeitung

  1. temperatureunder heating for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  4. customAfter removal of the drying agent
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; hexane-ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-d12b3fd6fb0c46a6913becc3e3446dfe
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06281355B1

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