4-Fluoroaniline → 3-(4-Fluorophenylamino)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

反応式

[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]([C:14]2([CH3:17])[CH2:16][O:15]2)=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1.Cl([O-])(=O)(=O)=O.[Na+]>C(#N)C>[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][CH2:16][C:14]([OH:15])([CH3:17])[C:12]([NH:11][C:4]2[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([CH3:1])[CH:3]=2)=[O:13])=[CH:21][CH:20]=1

参加物

実験手順

A mixture of 2-methyloxirane-2-carboxylic acid (3-methyl-4-nitrophenyl)amide (0.2 g, 0.85 mmol), 4-fluoroaniline (0.18 g, 1.7 mmol) and sodium perchlorate (0.21 g, 1.7 mmol) in 2 ml of acetonitrile was boiled under reflux for 6 hours. After a workup of the reaction mixture, the crude product was purified by flash chromatography (dichloromethane-1% methanol). 1H NMR (400 MHz, DMSO-d6): 1.41 (3H, s), 2.51 (3H, s), 3.10 (1H, dd, J=12.7 Hz, J=4.6 Hz), 3.41 (1H, dd, J=12.7 Hz, J=7.7 Hz), 5.26 (1H, m), 6.02 (1H, s), 6.62-6.66 (2H, m), 6.84-6.89 (2H, m), 7.79-7.83 (2H, m), 8.02 (1H, d, J=8.9 Hz), 9.99 (1H, s).