Synthesis of 2-[2-(tert-butoxycarbonyl)-3-(acyl)guanidino]ethylamine salts for convergent introduction of acyl guanidines. (11th April 2022)

• Record Type: Journal Article
• Authors: Boer, Gareth E.; Hickey, Shane M.; Elliott, Alysha G.; Pfeffer, Frederick M.
• Is Part Of: New journal of chemistry. Volume 46:Number 17(2022)
• Page Start: 8131
• Page End: 8137
• Publication Date: 2022-04-11
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj01510b
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : A series of acylguanidines with pre-installed ethylamino linkers are described that can be incorporated into larger structures through amide coupling. Abstract : Convergent, late-stage introduction of acylguanidine moieties is a useful strategy for the rapid development of novel compounds containing functionalised guanidines. As such, robust methodology for suitable acylguanidine building blocks is required. Here the synthesis of a range of 2-[2-( tert -butoxycarbonyl)-3-(acyl)guanidino]ethylamine salts is reported using the reaction of readily prepared acyl substituted S -methylisothioureas with ethylenediamine then conversion of these aminoethylacylguanidines to salts (using HCl or MsOH). A wide range of acyl groups were tolerated, with the desired salts being isolated in good yields (52–86% over two steps). Introduction of one of the new acylguanidine reagents to an organic scaffold was readily accomplished to generate a new antimicrobial agent.