Late-Stage Chloride Displacements Enable Access to Peptoids with -Inducing Alkylammonium Side Chains.

Org Lett

Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, United States.

Published: August 2023

The synthesis of peptoids possessing multiple -inducing monomers with alkylammonium side chains is reported, where chloropropyl side chains are diversified on a solid support by late-stage S2 displacements with amines. The conditions were optimized for a wide variety of primary, secondary, and tertiary alkyl amine nucleophiles. We also demonstrated that multiple chloride displacements could be achieved on sequences possessing -inducing -aryl- and -imino glycine monomers.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10903636PMC
http://dx.doi.org/10.1021/acs.orglett.3c02393DOI Listing

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