Diisopropylethylamine → (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxyphenyl)carbamate
반응식
[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]참가 물질
반응물 3
생성물 1
시약·촉매·용매 3
반응 조건
- 온도
- 100 °C
실험 절차
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.
후처리
- 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)
출처 및 근거
- ORD 기록
- ord-f390a318cb874e12b5dbe5051969b40f
- 출처 데이터셋
- uspto-grants-2007_08
- 특허 번호
- US07262212B2
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