Reaktion #684978

Reaktionsgleichung

HOAt

EDC

racemic ketoprofen

6-sulfamoylhexanoic acid ethyl ester

→

title compound

Ausbeute 46.3%

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

Ausbeute 46.3%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeresulted
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 3 d
3. 3
   WaschenThe mixture was washed with 1N aqueous HCl
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification by column chromatography

Vorschrift

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.

Quelle