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Synfacts 2023; 19(06): 0633
DOI: 10.1055/s-0042-1752673
Peptide Chemistry

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

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Li B, *, Bemish R, Buzon RA, Chiu CK.-F, Colgan ST, Kissel W, Le T, Leeman KR, Newell L, Roth J. Pfizer Global Research and Development, Groton, USA
Aqueous Phosphoric Acid as a Mild Reagent for Deprotection of the t-Butoxycarbonyl Group.

Tetrahedron Lett. 2003;
44: 8113-8115
DOI: 10.1016/j.tetlet.2003.09.040.
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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.


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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.


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Publication History

Article published online:
11 May 2023

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