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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 1158295
ノート
印刷プレビュー

反応式

HRID 1158295 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

HCID 866043773-(4-trifluoromethylphenyl)-2-propenyl (S)-4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate
収率 51%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cacf841fe9254634981af9abcebb8b66
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07807843B2

反応ノート

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