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Facile synthesis and cleavage of imidazolidines in a novel protection strategy for the preparation of peptides containing a reduced amide bioisostere

✍ Scribed by Jun Zhao; Vatee Pattaropong; Yongying Jiang; Longqin Hu

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
319 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Unsymmetrical imidazolidines were obtained in 75-91% yield by treating monoalkoxycarbonyl vicinal diamines at room temperature with aqueous 37% formaldehyde in the presence of Montmorillonite KSF as a solid catalyst. The imidazolidines were shown to be useful intermediates in a novel protection strategy for the synthesis of peptide analogues containing a reduced glycine amide bioisostere. The imidazolidine intermediate was cleaved conveniently and efficiently by 50% TFA in methylene chloride.

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