Water → 3-(4-Trifluoromethylphenyl)-2-propenyl(s)-4-{3-[2-(2-chloro-6-nitrophenylthio)-4-nitroimidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate

HRID 1092874Notes

Reaction equation

HRID 1092874 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[S:16][C:17]1[N:18]([CH2:25][C@:26]2([CH3:29])[CH2:28][O:27]2)[CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[N:21]=1.[N:30]1([C:36]([O:38][CH2:39][CH:40]=[CH:41][C:42]2[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][CH:43]=2)=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.O>C(OCC)(=O)C>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[S:16][C:17]1[N:18]([CH2:25][C@:26]([OH:27])([CH3:29])[CH2:28][N:33]2[CH2:32][CH2:31][N:30]([C:36]([O:38][CH2:39][CH:40]=[CH:41][C:42]3[CH:47]=[CH:46][C:45]([C:48]([F:50])([F:51])[F:49])=[CH:44][CH:43]=3)=[O:37])[CH2:35][CH2:34]2)[CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 665893003-(4-Trifluoromethylphenyl)-2-propenyl piperazine-1-carboxylateHCID 86604374(R)-2-(2-chloro-6-nitrophenylthio)-1-(2-methyl-2-oxiranylmethyl)-4-nitroimidazole

Product 1

HCID 866043733-(4-Trifluoromethylphenyl)-2-propenyl(s)-4-{3-[2-(2-chloro-6-nitrophenylthio)-4-nitroimidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylateYield 89.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N,N-Dimethylformamide (0.25 ml) solution of (R)-2-(2-chloro-6-nitrophenylthio)-1-(2-methyl-2-oxiranylmethyl)-4-nitroimidazole (55 mg) and 3-(4-trifluoromethylphenyl)-2-propenyl piperazin-1-carboxylate (51 mg) was stirred at 60° C. for 1 day. To the reaction mixture was added water and ethyl acetate, the organic layer was taken by separation. The ethyl acetate layer was washed with water and an aqueous solution being saturated with sodium chloride, then dried over anhydrous sodium sulfate. The residue obtained by removal of the solvent by distillation was purified by use of a thin layer chromatography (eluent: dichloromethane/methanol=30/1), there was obtained 3-(4-trifluoromethylphenyl)-2-propenyl(S)-4-{3-[2-(2-chloro-6-nitrophenylthio)-4-nitroimidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate (91 mg, yield: 87%) as yellow amorphous product.

Workup

  1. customthe organic layer was taken by separation
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by removal of the solvent by distillation
  5. customwas purified by use of a thin layer chromatography (eluent: dichloromethane/methanol=30/1)

Sources & evidence

ORD record
ord-85b5ba492bcb4da89fb0730f7f96bd68
Source dataset
uspto-grants-2012_03
Patent number
US08129544B2

Reaction notes

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