Reaktion #155808

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 85.8%

Lösungsmittel

water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane
2. 2
   WaschenThe extract was washed with saturated brine
3. 3
   Trocknendried over anhydrous sodium sulfate
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→0:100→dichloromethane:methanol=10:1)

Vorschrift

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.

Quelle