Reaction #684978

Reaction equation

HOAt

EDC

racemic ketoprofen

6-sulfamoylhexanoic acid ethyl ester

→

title compound

Yield 46.3%

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

Yield 46.3%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otherresulted
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 3 d
3. 3
   WashThe mixture was washed with 1N aqueous HCl
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated
6. 6
   OtherPurification by column chromatography

Procedure

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