Reaktion #417803

Reaktionsgleichung

6-(N-carbobenzoxy-L-phenylalanylamino)quinoline

allyl bromide

dimethylformamide

→

XVI

Ausbeute 39.0%

1-Allyl-6-(N-carbobenzoxy-L-phenylalanylamino) quinoline Bromide

Ausbeute 39.0%

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto react at room temperature for 48 h and at 50° C. for 12 h
2. 2
   SonstigeThe compound was purified
3. 3
   workup.DISSOLUTIONby dissolving the solid in water at 50° C.
4. 4
   Filtrationfiltering the undissolved material

Vorschrift

A solution consisting of 100 mg (0.235 mmol) of 6-(N-carbobenzoxy-L-phenylalanylamino)quinoline (Brynes, et al., 1981), 204 1 of allyl bromide, and 0.5 ml of dimethylformamide was allowed to react at room temperature for 48 h and at 50° C. for 12 h. Crude product was isolated by precipitation with ether followed by two ether washes. The compound was purified by dissolving the solid in water at 50° C., filtering the undissolved material and lyophilizing to obtain pure XVI. Recrystallization from ethanol/ethyl acetate yielded 50 mg (39% yield): mp 160° C. decomposes, 219° C. melts;Rf(E)=0.08. Fast atom bombardment mass spectrum of XVI: calculated for MW (466)+Br-. Found 466 (M=).

Quelle