Ethyl Acetate → 5-(2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-pentanoic acid methyl ester

HRID 448877ノート

反応式

HRID 448877 の反応式
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:19]1[CH:20]=[N:21][C:22]([Cl:26])=[CH:23][C:24]=1[CH3:25].C[CH:28]([CH2:33][CH2:34][CH3:35])[C:29]([O:31]Br)=[O:30].[C:36]([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH3:36][O:31][C:29](=[O:30])[CH2:28][CH2:33][CH2:34][CH2:35][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:8]([C:6](=[O:7])[C:5]1[CH:17]=[CH:18][C:2]([Cl:1])=[C:3]([C:19]2[CH:20]=[N:21][C:22]([Cl:26])=[CH:23][C:24]=2[CH3:25])[CH:4]=1)[CH3:9]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 866425714-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamideHCID 86642572Bromo methylvalerate

生成物 1

HCID 593703575-(2-{[4-Chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-pentanoic acid methyl ester収率 35.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide (108 mg, 0.28 mmol), bromo methylvalerate (60 μL, 0.42 mmol) and K2CO3 (116 mg, 0.84 mmol) in DMF (1 mL) was stirred at room temperature for 14 hrs. Ethyl acetate was added and the combined organic layers were washed with water, dried over MgSO4, then purified by silica gel column chromatography eluted with ethyl acetate/hexane (1/4) up to 1/3 to yield 5-(2-{[4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenoxy)-pentanoic acid methyl ester 12-1 (50 mg). MS [M+H]+: 501; tR=8.52 min. (method 1)

後処理

  1. washthe combined organic layers were washed with water
  2. dry with materialdried over MgSO4
  3. custompurified by silica gel column chromatography
  4. washeluted with ethyl acetate/hexane (1/4) up to 1/3

出典と根拠

ORDレコード
ord-1d740461d29e48059573328d3896c70b
出典データセット
uspto-grants-2013_07
特許番号
US08481738B2

反応ノート

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