Development of Mild Conditions for the Deprotection of the tert-Butoxycarbonyl Protecting Group

Key words

phosphoric acid - deprotection - tert-butoxycarbonyl group - peptide synthesis

Significance

Protecting groups play an essential role in organic synthesis. Among them, the tert-but­oxycarbonyl (Boc) protecting group is unique and widely used in synthetic chemistry. Hence, there is a high demand for the development of simple and mild methods for the protection and deprotection of Boc groups. In 2003, the authors found aqueous phosphoric acid to be a mild reagent for the deprotection of the Boc group.

Comment

Aqueous phosphoric acid is efficiently used for the deprotection of the Boc group in various Boc-protected amine compounds. This protocol is mild, practically simple, and showcases high functional group tolerance. Furthermore, it preserves the stereochemical integrity of N-Boc amino acids.

Publikationsverlauf

Artikel online veröffentlicht:
11. Mai 2023