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Water → 4-(Benzo[d]isoxazol-3-ylcarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2262874
ノート
印刷プレビュー

反応式

HRID 2262874 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([N:10]([C:19]([O:21]CC(Cl)(Cl)Cl)=O)C(OCC(Cl)(Cl)Cl)=O)=[N:2]1.C(N(C(C)C)CC)(C)C.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37].O>CS(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][C:19]([N:46]2[CH2:45][CH2:44][N:43]([C:41]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:42])[CH2:48][CH2:47]2)=[O:21])=[N:2]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 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86625471Bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate

生成物 1

HCID 687244984-(Benzo[d]isoxazol-3-ylcarbamoyl)-piperazine-1-carboxylic acid tert-butyl ester収率 33.2%

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

実験手順

A solution of bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate (3.00 g, 6.19 mmol), diisopropylethylamine (1.08 ml, 6.19 mmol) and 1-(tert-butoxycarbonyl)piperazine (2.30 g, 12.4 mmol) in dimethyl sulfoxide (20 ml) was stirred at 70° C. for 2 hours. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was crystallized from hexane, which was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and then recrystallized from a mixed solvent of hexane and ethyl acetate to give 710 mg (33.2%) of the desired product.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was crystallized from hexane, which
  6. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  7. customrecrystallized from a mixed solvent of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-aae8247b278b48bab8dc9e014726dfba
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07851473B2

反応ノート

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