Reaktion #1618754

Reaktionsgleichung

triphenylphosphine

imidazole

diethyl azodicarboxylate

{2-[5-acetylamino-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}-[4-(4-amino(dimethanesulfonyl)phenyl)butyl] carbamic acid tert-butyl ester

triphenylphosphine

imidazole

diethyl azodicarboxylate

→

title compound

{2-[2-(3,5-dimethylphenyl)-5-(5-methyltetrazol-1-yl)-1H-indol-3-yl]-ethyl}-[4-(4-amino(dimethanesulfonyl)phenyl) butyl]carbamic acid tert-butyl ester

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturto reflux on an oil bath
3. 3
   SonstigeAfter an additional 3 hours reaction time
4. 4
   Temperaturthe pot was cooled to room temperature
5. 5
   Sonstigethe reaction mixture applied directly to a silica gel column for purification by flash chromatography (hexane:ethyl acetate, 2:3)

Vorschrift

To a solution of {2-[5-acetylamino-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}-[4-(4-amino(dimethanesulfonyl)phenyl)butyl] carbamic acid tert-butyl ester (30 mg in 1.5 mL dry methylene chloride) was added in order 22.8 mg triphenylphosphine, 6.3 mg imidazole, 20.7 mg zinc azide(pyridine complex) and 0.014 mL diethyl azodicarboxylate and the mixture stirred at room temperature. After 4 hours additional portions of triphenylphosphine (11.3 mg), imidazole (3.5 mg), zinc azide•2 pyridine (11 mg) and diethyl azodicarboxylate (0.007 mL) were added and the mixture heated to reflux on an oil bath. After an additional 3 hours reaction time, the pot was cooled to room temperature and the reaction mixture applied directly to a silica gel column for purification by flash chromatography (hexane:ethyl acetate, 2:3) to give the title compound (26 mg).

Quelle