4-Methylmorpholine → Z-Trp-Gly-OCH3

Participants

Reaction Steps

At 0° C. there were added while stirring 6.5 ml of N-methyl morpholine to a mixture of 3.35 g (0.05 mol) of Z-Trp-OH and 1.25 g of H-Gly-OMe. Into the solution obtained there were added dropwise at the temperature specified, while stirring, 4 g of methylethylphosphinic acid anhydride. The mixture was allowed to stand at room temperature for 10 hours and the solvent was separated by distillation in vacuo at room temperature. The residue was taken up by a mixture of 25 ml of water and 70 ml of ethyl acetate, the ethyl acetate extract was separated and the aqueous solution was extracted twice using each time 10 ml of ethyl acetate. The combined ethyl acetate extracts were washed twice using each time 7 ml of water, a 5% potassium sulfate solution (until an acid reaction took place) and a saturated NaHCO3 solution until a slightly alkaline reaction took place. Upon drying over magnesium sulfate and clearing with active carbon, the solvent was largely separated by distillation in vacuo and the residue was digested with diisopropyl ether.

Provenance & Evidence