Réaction #684978

Équation de réaction

HOAt

EDC

racemic ketoprofen

6-sulfamoylhexanoic acid ethyl ester

→

title compound

Rendement 46.3%

6-[2-(3-Benzoylphenyl)propionylsulfamoyl]hexanoic acid

Rendement 46.3%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autreresulted
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 3 d
3. 3
   LavageThe mixture was washed with 1N aqueous HCl
4. 4
   Séchagedried over MgSO4
5. 5
   Concentrationconcentrated
6. 6
   AutrePurification by column chromatography

Mode opératoire

To a suspension of racemic ketoprofen (3.81 g, 15.0 mmol) in dichloromethane (50 ml) were added HOAt (2.04 g, 15.0 mmol) and EDC (2.88 g, 15.0 mmol), and the mixture was stirred until a clear solution resulted. To this solution was added a solution of 6-sulfamoylhexanoic acid ethyl ester (2.23 g, 10.0 mmol) and DI PEA (2.56 ml) in dichloromethane, and the mixture was stirred at room temperature for 3 d. The mixture was washed with 1N aqueous HCl, dried over MgSO4, and concentrated. Purification by column chromatography yielded 2.0 g (44%) of the title compound. An analytical sample was obtained by preparative HPLC.

Source