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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 2221397
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Reaktionsgleichung

Reaktionsgleichung von HRID 2221397
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
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Komponenten

6

Edukt 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

Produkt 1

HCID 86604373
3-(4-Trifluoromethylphenyl)-2-propenyl(s)-4-{3-[2-(2-chloro-6-nitrophenylthio)-4-nitroimidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate
Ausbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a72a4031007848779c4dee38e2170bf7
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07368579B2

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