Reacción #155808

Ecuación de reacción

compound 5

4-[([(benzyloxy)carbonyl]{4-[(tert-butoxycarbonyl)amino]butyl}amino)methyl]benzoic acid

compound 2

N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amine

1-hydroxybenzotriazole

1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride

diisopropylethylamine

→

title compound

Rendimiento 85.8%

Phenylmethyl({4-[(bis{[1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-2-yl]methyl}amino)carbonyl]phenyl}methyl)[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)butyl]carbamate

Rendimiento 85.8%

Disolventes

water

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with dichloromethane
2. 2
   LavadoThe extract was washed with saturated brine
3. 3
   Secadodried over anhydrous sodium sulfate
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→0:100→dichloromethane:methanol=10:1)

Procedimiento

To a solution of the compound 5 (137 mg) in dichloromethane (3 mL), the compound 2 (131 mg), 1-hydroxybenzotriazole (69 mg), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (86 mg) and diisopropylethylamine (105 μl) were added. The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was added by water and then extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→0:100→dichloromethane:methanol=10:1) to obtain the title compound (225 mg) having the following physical properties.

Fuente