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

HRID 651584Notes

Reaction equation

HRID 651584 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 54546355N-(2-nitrophenyl)-(2-cyanophenyl)alanine dihexylamideYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d12b3fd6fb0c46a6913becc3e3446dfe
Source dataset
uspto-grants-2001_08
Patent number
US06281355B1

Reaction notes

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