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Water → 3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate

HRID 2221399
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Reaktionsgleichung

Reaktionsgleichung von HRID 2221399
CN(C)C=O.[N+:6]([C:9]1[N:10]=[C:11](SC2C=CC([N+]([O-])=O)=CC=2)[N:12]([CH2:14][C@:15]([OH:40])([CH3:39])[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH:27]=[CH:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)=[O:24])[CH2:19][CH2:18]2)[CH:13]=1)([O-:8])=[O:7].CC(C)([O-])C.[Na+].O>ClCCl.C(OCC)(=O)C.CO.C(OCC)(=O)C>[CH3:39][C@@:15]1([CH2:16][N:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][CH2:26][CH:27]=[CH:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:36])([F:38])[F:37])=[CH:31][CH:30]=3)=[O:24])[CH2:21][CH2:22]2)[O:40][C:11]2=[N:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:13][N:12]2[CH2:14]1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 23676156Sodium t-butoxideHCID 866043693-(4-Trifluoromethylphenyl)-2-propenyl(s)-4-{3-[4-nitro-2-(4-nitrophenylthio)imidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate

Produkt 1

HCID 86604377
3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate
Ausbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21901258Dichloromethane ethyl acetate methanolLösungsmittel

Versuchsvorschrift

To N,N-dimethylformamide (1 ml) solution of 3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-{3-[4-nitro-2-(4-nitrophenylthio)imidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate (100 mg) was added sodium tert-butoxide (19 mg) at 0° C., and stirred at the same temperature for 20 minutes. To the reaction mixture was added water and ethyl acetate, the organic layer was taken by separation. The ethyl acetate layer was washed with an aqueous solution of 5% potassium carbonate, 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 basic silica gel chromatography (eluent: dichloroethane/ethyl acetate=9/1) and a slica gel column chromatography (eluent: dichloromethane/ethyl acetate/methanol=20/20/1), there was obtained 3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo-[2,1-b]oxazol-2-ylmethyl)piperazin-1-carboxylate (40 mg, yield: 54%) as yellow amorphous product.

Aufarbeitung

  1. customthe organic layer was taken by separation
  2. washThe ethyl acetate layer was washed with an aqueous solution of 5% potassium carbonate, 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 basic silica gel chromatography (eluent: dichloroethane/ethyl acetate=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-20bd4cb7bdd04c66b607ecb63822aaca
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07368579B2

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