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

HRID 2262874
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HRID 2262874 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86625471Bis(2,2,2-trichloroethyl) 1,2-benzisoxazol-3-ylimidodicarbonate

생성물 1

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

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aae8247b278b48bab8dc9e014726dfba
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07851473B2

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