Pyridine → 2768-53-8

Participants

Reaction Steps

A solution of 0.223 g (0.001 mol) of N-benzyloxycarbonylalanine (Z-Ala), 0.08 g (0.001 mol) of pyridine and 0.256 g (0.001 mol) of DSC in 10 ml of dimethylformamide (DMF) 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 admixed with ethyl acetate and washed with aqueous 4% NaHCO3, with 1 N-HCl and with a saturated aqueous solution of sodium chloride. The solution so treated was then distilled to remove the ethyl acetate, leaving a solid residue. This 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 DMF, and the admixture so obtained was stirred at ambient temperature for 24 hours. Subsequently, the resultant reaction mixture was admixed with ethyl acetate, washed with aqueous 4% NaHCO3, with 1 N-HCl and with a saturated aqueous solution of sodium chloride to remove the liberated N-hydroxysuccinimide, followed by drying over anhydrous sodium sulfate. The dried solution was filtered and the filtrate was distilled to remove the solvent, affording a colorless crystalline substance. Recrystallization of this crystalline substance from methylene chloride-ethyl ether gave 0.321 g of N-benzyloxycarbonylalanyl-phenylalanine (Z-Ala-Phe-OH) as a colorless crystalline substance. Yield 86%.

Provenance & Evidence