Acetone → tert-butyl (Z)-4-{4-[(perfluorophenoxy)carbonyl]-2-(prop-1-en-1-yl)phenyl}piperazine-1-carboxylate

HRID 1038533노트

반응식

HRID 1038533 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=2/[CH:23]=[CH:24]\[CH3:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)=O.[F:30][C:31]1[C:36](O)=[C:35]([F:38])[C:34]([F:39])=[C:33]([F:40])[C:32]=1[F:41].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.O>[F:30][C:31]1[C:32]([F:41])=[C:33]([F:40])[C:34]([F:39])=[C:35]([F:38])[C:36]=1[O:19][C:18]([C:17]1[CH:21]=[CH:22][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)=[C:15](/[CH:23]=[CH:24]\[CH3:25])[CH:16]=1)=[O:20]

참가 물질

7

반응물 4

HCID 180AcetoneHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 66598895(Z)-4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-3-(prop-1-en-1-yl)benzoic acid

생성물 1

HCID 86647187tert-butyl (Z)-4-{4-[(perfluorophenoxy)carbonyl]-2-(prop-1-en-1-yl)phenyl}piperazine-1-carboxylate수율 95%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

(Z)-4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-3-(prop-1-en-1-yl)benzoic acid (108 mg, 0.267 mmol) was dissolved in ethyl acetate:acetone=4:1 (5.7 mL). At room temperature, pentafluorophenol (59 mg, 0.320 mmol) and N,N′-dicyclohexylcarbodiimide (66 mg, 0.320 mmol) were added sequentially, and the mixture was stirred at room temperature for 10 hours. The reaction solution was added water, extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (129 mg (yield 95%)) was obtained as a white crystal.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

출처 및 근거

ORD 기록
ord-697fe3c805b24cee81438b07c3744455
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551985B2

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