Реакция #684978

Уравнение реакции

HOAt

EDC

racemic ketoprofen

6-sulfamoylhexanoic acid ethyl ester

→

title compound

Выход 46.3%

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

Выход 46.3%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеresulted
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 3 d
3. 3
   ПромывкаThe mixture was washed with 1N aqueous HCl
4. 4
   Сушкаdried over MgSO4
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеPurification by column chromatography

Методика

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.

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