Amidation is one of the most extensively studied synthetic methodologies in chemistry. However, it can be sometimes problematic because of undesired side reactions especially when the reactivity of the two coupling partners is challenged sterically or electronically. Aminoisobutyric acid(AIB) is a popular building block and often a strategical synton in drug design as it provides resistance to hydrolysis in vivo metabolism. Despite its utility in medicinal chemistry, peptide bond formation with AIB is found to be difficult due to the steric hindrance by gem-dimethyl groups and rapid formation of oxazolone intermediate via an intramolecular cyclization. In order to solve this problem, we developed an oxazolone-mediated methodology for peptide bond formation of AIB. Amidation reactions were performed with various amines to examine the reactivity of the oxazolone originated from a protected-AIB-OH.

Amidation of aminoisobutyric acid using oxazolone as a synthetic tool

251st National Meeting (2016)

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