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Synfacts 2023; 19(07): 0738
DOI: 10.1055/s-0042-1752702
Peptide Chemistry

Selective Deprotection of tert-Butyl Ester Groups in N-Boc-Protected Amino Acid tert-Butyl Esters

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Marcantoni E, *, Massaccesi M, Torregiani E, Bartoli G, *, Bosco M, Sambri L. University of Camerino and University of Bologna, Italy
Selective Deprotection of N-Boc-Protected tert-Butyl Ester Amino Acids by the CeCl3·7H2O–NaI System in Acetonitrile.

J. Org. Chem. 2001;
66: 4430-4432
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Key words

protecting groups - selective deprotection - cerium(III) chloride - sodium iodide

Significance

Most commonly in amino acids, the amine group is protected with a Boc group and the carboxylic acid functionality is protected with a tert-butyl group. Hence, selective deprotection of a tert-butyl ester group in presence of N-Boc is highly challenging. In 2001, the authors developed a ­cerium(III) chloride and NaI-mediated selective deprotection of tert-butyl esters in the presence of N-Boc-protected amino acids.


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Comment

Selective deprotection of tert-butyl ­esters in the presence of N-Boc-protected amino acids with the help of cerium(III) chloride and NaI proceeded smoothly to afford the desired products in good yield. This protocol is practically very simple, cost-effective, and showcases a broad functional group tolerance.


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Publication History

Article published online:
16 June 2023

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