Preparation of polymers containing the 1,3,4‐oxadiazoline‐5‐thione structure and their application to the activation of N‐protected α‐amino acids

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Abstract
Two new monomers with pendent 1,3,4‐oxadiazoline‐5‐thione structures were prepared. Homopolymerization of 2‐isopropenyl‐1,3,4‐oxadiazoline‐5‐thione (V) and copolymerization with styrene (M1)(r1 = 0.02, r2 = 1.56, Q = 4.12, e = 1.06) were examined. Further, 2‐(4‐methacryloylaminophenyl)‐1,3,4‐oxadiazoline‐5‐thione (VIII) having a phenylcarbamoyl group between the isopropenyl and 1,3,4‐oxadiazoline‐5‐thione ring as a spacer was also synthesized and polymerized. The resultant polymers were allowed to react with N‐protected α‐amino acids such as Z‐AlaOH, Z‐LeuOH and Z‐PheOH by the DCC method. The polymers containing amino acids thus obtained were reacted with ethyl glycinate to give the corresponding dipeptides in excellent yields without racemization.

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