Reacción #5682

Ecuación de reacción

5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

trifluoroacetic acid

anisole

→

5-(L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Rendimiento 32.2%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONThe trifluoroacetic acid is almost distilled off under reduced pressure
2. 2
   Extracciónthe mixture is extracted with dichloromethane
3. 3
   LavadoThe dichloromethane layer is washed with water
4. 4
   Secadodried over magnesium sulfate
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate)

Procedimiento

A uniform solution of 5-(N-tert-butoxycarbonyl-L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.27 g), trifluoroacetic acid (2.5 ml) and anisole (0.6 ml) is stirred at room temperature for 2 hours. The trifluoroacetic acid is almost distilled off under reduced pressure, and the residue is acidified with an 0.2 N aqueous sodium hydroxide solution, and the mixture is extracted with dichloromethane. The dichloromethane layer is washed with water, dried over magnesium sulfate and concentrated. The resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate) to give Isomer A (0.34 g) and Isomer B (0.35 g) of 5-(L-methionyloxy)-7-chloro-1-[2-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine.

Fuente