Reacción #47833

Ecuación de reacción

triethylamine

cyclohexylamine

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid

6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic Acid

water

→

titled compound

Rendimiento 20.0%

6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic Acid Cyclohexylamide

Rendimiento 20.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat 10° C
2. 2
   workup.STIRRINGstirred for additional 1 hr in a water bath
3. 3
   Otrothe reaction
4. 4
   Lavadothe mixture washed with sodium bicarbonate
5. 5
   Extracciónextracted with dichloromethane
6. 6
   OtroThe organic layer was separated
7. 7
   Secadodried over anhydrous MgSO4
8. 8
   Concentraciónconcentrated under a reduced pressure
9. 9
   OtroThe resulting residue was purified by flash chromatography

Procedimiento

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid (100 mg, 0.38 mmol) obtained in Step 2 was dissolved in dichloromethane, and triethylamine (175 μl, 1.25 mmol) and cyclohexylamine (43 μl, 0.38 mmol) were added thereto at 10° C. Then, bis(2-oxo-3-oxazoline)phosphoryl chloride (100 mg, 0.38 mmol) was further added thereto, stirred for 10˜20 minutes at RT, and then stirred for additional 1 hr in a water bath. After water was added to complete the reaction, the mixture washed with sodium bicarbonate and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4, concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 26 mg of the titled compound (yield: 20.0%) as a red solid.

Fuente