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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 2221401
Notes
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Reaction equation

HRID 2221401 reaction equation
CN(C)C=O.ClC1C=CC=C([N+]([O-])=O)C=1S[C:17]1[N:18]([CH2:25][C@:26]([OH:51])([CH3:50])[CH2:27][N:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][CH:38]=[CH:39][C:40]3[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=3)=[O:35])[CH2:30][CH2:29]2)[CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[N:21]=1.CC(C)([O-])C.[Na+].O>C(OCC)(=O)C>[CH3:50][C@@:26]1([CH2:27][N:28]2[CH2:29][CH2:30][N:31]([C:34]([O:36][CH2:37][CH:38]=[CH:39][C:40]3[CH:45]=[CH:44][C:43]([C:46]([F:47])([F:49])[F:48])=[CH:42][CH:41]=3)=[O:35])[CH2:32][CH2:33]2)[O:51][C:17]2=[N:21][C:20]([N+:22]([O-:24])=[O:23])=[CH:19][N:18]2[CH2:25]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 23676156Sodium t-butoxideHCID 866043733-(4-Trifluoromethylphenyl)-2-propenyl(s)-4-{3-[2-(2-chloro-6-nitrophenylthio)-4-nitroimidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate

Product 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
Yield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To N,N-dimethylformamide (0.9 ml) solution of 3-(4-trifluoromethylphenyl)-2-propenyl (S)-4-{3-[2-(2-chloro-6-nitrophenylthio)-4-nitroimidazol-1-yl]-2-hydroxy-2-methylpropyl}piperazin-1-carboxylate (89 mg) was added sodium tert-butoxide (16 mg) at 0° C., and stirred at the same temperature for 30 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 thin layer chromatography (eluent: dichloromethane/ethyl acetate/methanol=15/15/1), 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 (32 mg, yield: 51%) as pale yellow amorphous product.

Workup

  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 thin layer chromatography (eluent: dichloromethane/ethyl acetate/methanol=15/15/1)

Sources & evidence

ORD record
ord-21cf8dcd94444af2824def6b582920f9
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368579B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes