Diisopropylethylamine → (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl N-methyl-N-(4-trifluoromethoxyphenyl)carbamate
Reaction equation
[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]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
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.
Workup
- 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)
Sources & evidence
- ORD record
- ord-f390a318cb874e12b5dbe5051969b40f
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07262212B2
Reaction notes
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