تفاعل #323682

معادلة التفاعل

dibenzyl N-(N-tert-butoxycarbonyl-L-valyl)glutamate

anisole

triethylamine

n-octanoyl chloride

→

dibenzyl N-(N-octanoyl-L-valyl)-L-glutamate

المذيبات

trifluoroacetic acid

benzene

tetrahydrofuran

chloroform

ظروف التفاعل

المعالجة

1. 1
   أخرىEvaporation of trifluoroacetic acid under reduced pressure
2. 2
   أخرىgave a residue which
3. 3
   workup.DISTILLATIONBenzene was distilled off
4. 4
   أخرىto leave crude dibenzyl N-(L-valyl)-L-glutamate, which
5. 5
   غسيلthe organic layer was washed with 1N hydrochloric acid solution, aqueous sodium carbonate solution and brine successively
6. 6
   تجفيفdried over magnesium sulfate
7. 7
   أخرىAfter solvent was evaporated
8. 8
   أخرىthe residue was crystallized from ethyl acetate

الإجراء التجريبي

A solution of dibenzyl N-(N-tert-butoxycarbonyl-L-valyl)glutamate (1 g) and anisole (1 ml) in trifluoroacetic acid (2 ml) was stirred at 0° C. for 1 hour. Evaporation of trifluoroacetic acid under reduced pressure gave a residue which was taken up in benzene. Benzene was distilled off by using high vacuum pump. This operation was repeated three times to leave crude dibenzyl N-(L-valyl)-L-glutamate, which was dissolved in tetrahydrofuran (20 ml). To this solution was added triethylamine (1 ml) and n-octanoyl chloride (0.7 ml) at 0° C., and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with chloroform and the organic layer was washed with 1N hydrochloric acid solution, aqueous sodium carbonate solution and brine successively, dried over magnesium sulfate. After solvent was evaporated, the residue was crystallized from ethyl acetate to afford white amorphous powder of dibenzyl N-(N-octanoyl-L-valyl)-L-glutamate (600 mg).

المصدر