Glycine → N-[(Phenylmethoxy)carbonyl]-L-phenylalanylglycine

Participants

Reaction Steps

A solution of 0.299 g (0.001 mol) of N-benzyloxycarbonylphenylalanine (Z-Phe), 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-Phe (the free acid form) disappeared in the solution, the reaction solution was admixed with 0.075 g (0.001 mol) of glycine (Gly-OH) and 0.101 g (0.001 mol) of triethylamine, followed by stirring at ambient temperature for 24 hours. The resultant reaction mixture was concentrated to a small volume, 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 filtered and the filtrate was distilled to remove the solvent, affording a colorless crystalline substance. Recrystallization of this solid substance from ethyl acetate-petroleum ether gave 0.30 g of N-benzyloxycarbonylphenylalanylglycine (Z-Phe-Gly-OH) as a colorless crystalline substance. Yield 83.4%.

Provenance & Evidence