Reacción #684978

Ecuación de reacción

HOAt

EDC

racemic ketoprofen

6-sulfamoylhexanoic acid ethyl ester

→

title compound

Rendimiento 46.3%

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

Rendimiento 46.3%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroresulted
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 3 d
3. 3
   LavadoThe mixture was washed with 1N aqueous HCl
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated
6. 6
   OtroPurification by column chromatography

Procedimiento

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.

Fuente