N-TERT-BUTYLGLYOXYLICAMIDE, THE NEW REAGE NT FOR PEPTIDE SEGMENT COUPLING BY 4-COMPONENT REACTION

In contrast to the use of other aldehyd components, the Tetra Componen t Reactions (4 CR) of carboxyl acids and primary amines with combinati ons of N-tert-butylglyoxylicamide and isocyanides produce carbonamides that yield the desired stereochemically uniform condensation products . Often a further advantage of such products is their possibility of b eing oxidized selectively in the presence of CuCl2.2H(2)O/NEt(3)/air ( containing O-2) into the carbonamides of the here used carboxyl acids and primary amines. In particular, such products can thus be converted selectively into a-acylamino and peptide derivatives. In case of the modelpeptide phenylaceticbenzylamide 8a quantitative cleavage yields, in the course of the appropriate dipeptide derivatives (8b-8f) cleavag e yields of 56-81% are obtained.