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

Participants

Reaction Steps

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).

Provenance & Evidence