The Reaction of Amines with Amino Acid N-Carboxy Anhydrides

RECEIVED SEPTEMBER 11, 1956. 'l'hc i-cacli~ill uf :t~iiiiiei with S-carl~osyaiili).dritlcs of a-amiiio acids priiccctih lo yicl:l citliel- J til-eido ...
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KENNETHD. Iiorrr,~

The Reaction of Amines with Amino Acid N-Carboxy Anhydrides BY KENNETH 1).KOPPLE RECEIVED SEPTEMBER 11, 1956 'l'hc i-cacli~illuf : t ~ i i i i i e iwith S-carl~osyaiili).dritlcsof a-amiiio acids priiccctih lo yicl:l citliel- J til-eido Lieid (attack d l 1 1 1 ~ 2-carhonyl of the oxazolidinedioiic ring) or a n amino amide (attack at the 5-carbuiiyl Tile actual course of the reactioii is tlependent on the steric requirenieiits of the aniiiie, its cunceiitration aiid its basicity. 21 iiuniber of iiew ureido acids arc re1)orted.

The reaction of an a-amino acid hi-carboxy anhydride (4-alkyl-2,5-oxazolidinedio1ic, I, abbreviated here to NCAj with an amine may, in principle, take either of two paths, X or B. KCH---CO

r+ j A

)o 3- K,1