Pyridine → 2768-53-8

Participants

Reaction Steps

A solution of 0.223 g (0.001 mol) of N-benzyloxycarbonyl alanine (Z-Ala), 0.08 g (0.001 mol) of pyridine and 0.256 g (0.001 mol) of DSC in 10 ml of acetonitrile was stirred at ambient temperature. After silica gel TLC. showed that Z-Ala (the free acid form) disappeared in the solution, the reaction solution was concentrated to a small volume, and the concentrated solution was admixed with ethyl acetate and then washed with aqueous 4% NaHCO3, with 1 N-HCl and finally with a saturated aqueous solution of sodium chloride to remove the liberated N-hydroxysuccinimide. The solution so treated was distilled to remove the ethyl acetate. The resultant solid residue was admixed with a solution of 0.165 g (0.001 mol) of phenylalanine (Phe-OH) and 0.101 g (0.001 mol) of triethylamine in 20 ml of a mixed solvent of acetonitrile and water (4:6 by volume). 24 Hours later, the reaction solution was concentrated to a small volume, and the concentrated solution was admixed with ethyl acetate, washed with aqueous 4% NaHCO3, with 1 N-HCl and with a saturated aqueous solution of sodium chloride, followed by drying over anhydrous sodium sulfate. The dried solution was then filtered and the filtrate was distilled, affording a colorless crystalline substance. Recrystallization of this crystalline substance from methylene chloride-ethyl ether gave 0.34 g of N-benzyloxycarbonylalanyl-phenylalanine (Z-Ala-Phe-OH) as a colorless crystalline substance. Yield 90%.

Provenance & Evidence