Potassium Carbonate → 4-[2-(3-Chloro-4-methoxycarbonyl-phenoxy)-acetyl]-piperazine-1-carboxylic Acid Tert-butyl Ester

HRID 220854노트

반응식

HRID 220854 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[Cl:11].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26](=[O:29])[CH2:27]Br)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:13]([O:17][C:18]([N:20]1[CH2:21][CH2:22][N:23]([C:26](=[O:29])[CH2:27][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:12])=[C:5]([Cl:11])[CH:6]=2)[CH2:24][CH2:25]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 134988302-Chloro-4-hydroxy-benzoic acid methyl esterHCID 15829155tert-Butyl 4-(bromoacetyl)piperazine-1-carboxylate

생성물 1

HCID 575553524-[2-(3-Chloro-4-methoxycarbonyl-phenoxy)-acetyl]-piperazine-1-carboxylic Acid Tert-butyl Ester수율 100%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2-Chloro-4-hydroxy-benzoic acid methyl ester from example E41b (2.0 g, 10.9 mmol) and 4-(2-Bromo-acetyl)-piperazine-1-carboxylic acid tert-butyl ester from Example E41a (3.68 g, 12.0 mmol) in acetonitrile (30 ml) were treated with potassium carbonate (1.6 g, 11.5 mmol), and the mixture heated at reflux 18 h. before the solvents were removed in vacuo. The residue was adsorbed onto silica gel and purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% cyclohexane to 50% EtOAc:50% cyclohexane to 70% EtOAc:30% cyclohexane) to yield the title compound (4.5 g, 100%).

후처리

  1. temperaturethe mixture heated
  2. temperatureat reflux 18 h. before the solvents
  3. customwere removed in vacuo
  4. custompurified by flash chromatography on silica gel (eluant; 20% EtOAc:80% cyclohexane to 50% EtOAc:50% cyclohexane to 70% EtOAc:30% cyclohexane)

출처 및 근거

ORD 기록
ord-1f5b83af3f014c1daa9f0899622a978e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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