五氟苯酚 → N-[3-(N-cyclohexylcarbamoyl)phenyl]-4-hydroxy-3-methoxyphenylacetamide

HRID 7070

反应方程式

HRID 7070 反应方程式
[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

参与物

5

反应物 3

HCID 13041五氟苯酚HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐HCID 22019637N-(3-carboxyphenyl)-4-hydroxy-3-methoxyphenylacetamide

产物 1

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

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

反应条件

温度
25 °C

实验过程

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).

后处理

  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)

来源与证据

ORD记录
ord-e923ca3883c74703a1879eb55299542a
来源数据集
uspto-grants-2006_08
专利号
US07084176B2

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