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

HRID 7070
Notes
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Reaction equation

HRID 7070 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
25 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e923ca3883c74703a1879eb55299542a
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07084176B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes