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Synfacts 2022; 18(08): 0936
DOI: 10.1055/s-0041-1737694
Peptide Chemistry

Expeditious Deprotection of N-Benzyloxycarbonyl and N-Benzyl Derivatives

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Daga MC, Taddei M, *, Varchi G. Università degli Studi di Sassari, Italy
Rapid Microwave-Assisted Deprotection of N-Cbz and N-Bn Derivatives.

Tetrahedron Lett. 2001;
42: 5191-5194
DOI: 10.1016/S0040-4039(01)00969-8.
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Key words

microwave heating - deprotection - palladium catalysis - hydrogenation - amines - protecting groups

Significance

Protecting groups play an inherent role in organic synthesis, especially in peptide chemistry. Among them, Cbz and Bn are the most popular protecting groups for amines. Consequently, the development of methods for their installation and deprotection have gained attention. In 2001, Taddei and co-workers developed a microwave-assisted catalytic transfer hydrogenation for the deprotection of the N-Cbz and N-Bn derivatives.


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Comment

Deprotection of N-Cbz and N-Bn of amino acids, peptides, and amines proceeds efficiently by microwave-assisted transfer hydrogenation with Pd/C catalyst and ammonium formate reagent to afford the corresponding free amines in good yields. This method is mild, simple, rapid, and is also applicable to solid resin-supported substrates.


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Publication History

Article published online:
18 July 2022

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