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Pentafluorophenol → N-[3-(N-cyclohexylcarbamoyl)phenyl]-4-hydroxy-3-methoxyphenylacetamide

HRID 7070
ノート
印刷プレビュー

反応式

HRID 7070 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:22])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([O:20][CH3:21])[CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([OH:3])=O.F[C:24]1[C:29](O)=[C:28](F)[C:27](F)=[C:26](F)[C:25]=1F.Cl.C([N:38]=C=NCCCN(C)C)C>C(Cl)Cl>[CH:24]1([NH:38][C:1]([C:4]2[CH:5]=[C:6]([NH:10][C:11](=[O:22])[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([O:20][CH3:21])[CH:14]=3)[CH:7]=[CH:8][CH:9]=2)=[O:3])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 13041PentafluorophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22019637N-(3-carboxyphenyl)-4-hydroxy-3-methoxyphenylacetamide

生成物 1

HCID 22019598N-[3-(N-cyclohexylcarbamoyl)phenyl]-4-hydroxy-3-methoxyphenylacetamide収率 94.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

反応条件

温度
25 °C

実験手順

A mixture of N-(3-carboxyphenyl)-4-hydroxy-3-methoxyphenylacetamide (500 mg), pentafluorophenol (305 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (320 mg) and methylene chloride (10 ml) is stirred at 25° C. for 18 hours. The reaction solution is washed with water, and the solvent is evaporated under reduced pressure. To the residue are added ethyl acetate (10 ml) and cyclohexylamine (174 mg), and the mixture is heated with stirring at 60° C. for 18 hours. The solvent is evaporated and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (600 mg).

後処理

  1. washThe reaction solution is washed with water
  2. customthe solvent is evaporated under reduced pressure
  3. additionTo the residue are added ethyl acetate (10 ml) and cyclohexylamine (174 mg)
  4. temperaturethe mixture is heated
  5. stirringwith stirring at 60° C. for 18 hours
  6. customThe solvent is evaporated
  7. customthe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-e923ca3883c74703a1879eb55299542a
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07084176B2

反応ノート

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