We report a chelating hydrazone amide as a protecting group for carboxylic acids. Unlike most esters, 2-picolinaldehyde hydrazone amides are stable under acidic or basic hydrolytic conditions. However, hydrazone amides can be easily converted to the corresponding carboxylic acids via Ni-mediated hydrolysis. Orthogonal reactivities of the hydrazone amides and representative protecting groups were verified by control experiments and peptide synthesis, demonstrating that chelating hydrazone amides are highly useful protecting groups.
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