Sodium Acetate → 4-fluorobenzyl [3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-N-methylcarbamate

反応式

[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[CH3:10][N:11]([CH2:23][C:24]1([CH3:27])[CH2:26][O:25]1)[C:12](=[O:22])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.C([O-])(=O)C.[Na+]>C(O)C>[Cl:1][C:2]1[N:3]([CH2:27][C:24]([OH:25])([CH3:26])[CH2:23][N:11]([CH3:10])[C:12](=[O:22])[O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

参加物

実験手順

2-Chloro-4-nitro-1H-imidazole (0.953 g, 6.46 mmol) and 4-fluorobenzyl N-methyl-(2-methyloxiran-2-ylmethyl)carbamate (1.964 g, 7.75 mmol) were dissolved in ethanol (20 ml). To the solution, sodium acetate (0.583 g, 7.11 mmol) was added followed by stirring under reflux overnight. The reaction mixture was concentrated under reduced pressure. To the residue, ethyl acetate and water were added, and the solution was extracted with ethyl acetate. The organic phase was dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to afford 4-fluorobenzyl [3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl]-N-methylcarbamate (1.683 g, yield 65%) as a colorless oil.