Diisopropylethylamine → (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxyphenyl)carbamate
反応式
[CH3:1][N:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].C(N(CC)C(C)C)(C)C.[Cl:26][C:27]1[N:28]([CH2:35][C@:36]([OH:40])([CH3:39])[CH2:37][OH:38])[CH:29]=[C:30]([N+:32]([O-:34])=[O:33])[N:31]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][N:2]([C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]([F:14])([F:15])[F:16])=[CH:10][CH:11]=1)[C:3](=[O:4])[O:38][CH2:37][C@@:36]([OH:40])([CH3:39])[CH2:35][N:28]1[CH:29]=[C:30]([N+:32]([O-:34])=[O:33])[N:31]=[C:27]1[Cl:26]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 100 °C
実験手順
N-Methyl-N-(4-trifluoromethoxyphenyl)-carbamoyl chloride (1.33 g, 5.23 mmol), N,N-diisopropylethylamine (1.2 ml, 6.97 mmol) and 4-dimethylaminopyridine (85 mg, 0.70 mmol) were added to a suspension of (R)-2-chloro-1-(2,3-dihydroxy-2-methyl)propyl-4-nitroimidazole prepared in Example 10 (0.82 g, 3.48 mmol) in toluene (10 ml) followed by stirring at 100° C. for 5 hours. The reaction mixture was diluted with ethyl acetate, and the solution was washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1) to afford (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxyphenyl)carbamate (1.04 g, yield 65%) as a light yellow amorphous form.
後処理
- washthe solution was washed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=2/1)
出典と根拠
- ORDレコード
- ord-f390a318cb874e12b5dbe5051969b40f
- 出典データセット
- uspto-grants-2007_08
- 特許番号
- US07262212B2
反応ノート
読み込み中…