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

HRID 7070

반응식

HRID 7070 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e923ca3883c74703a1879eb55299542a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084176B2

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