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

HRID 220854ノート

反応式

HRID 220854 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-1f5b83af3f014c1daa9f0899622a978e
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

反応ノート

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