Reaktion #7166

Reaktionsgleichung

N-(3-carboxyphenyl)-4-hydroxy-3-methoxyphenylacetamide

pentafluorophenol

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

desired compound

Ausbeute 94.7%

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

Ausbeute 94.7%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle