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

HRID 1038533ノート

反応式

HRID 1038533 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-697fe3c805b24cee81438b07c3744455
出典データセット
uspto-grants-2013_10
特許番号
US08551985B2

反応ノート

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