Rapid and convenient semi-automated microwave-assisted solid-phase synthesis of arylopeptoids

Jakob Ewald Rasmussen; Marcello Massimo Boccia; John Nielsen; Claude Taillefumier; Sophie Faure; Thomas Hjelmgaard

doi:10.1016/j.tetlet.2014.08.119

Rapid and convenient semi-automated microwave-assisted solid-phase synthesis of arylopeptoids

Jakob Ewald Rasmussen^*, Marcello Massimo Boccia, John Nielsen, Claude Taillefumier, Sophie Faure, Thomas Hjelmgaard

^*Corresponding author for this work

Department of Chemistry

3 Citations (Scopus)

Abstract

A facile and expedient route to the synthesis of arylopeptoid oligomers (N-alkylated aminomethyl benz-amides) using semi-automated microwave-assisted solid-phase synthesis is presented. The synthesis was optimized for the incorporation of side chains derived from sterically hindered or unreactive amines and both ortho- and para-substituted arylo-backbones. By utilizing this optimized protocol a complex nonameric arylopeptoid was synthesized in less than 11 h, featuring a novel alternating ortho-, meta-, and para-substituted backbone pattern and a variety of chemically diverse and challenging side chains.

Original language	English
Journal	Tetrahedron Letters
Volume	55
Issue number	43
Pages (from-to)	5940-5943
Number of pages	4
ISSN	0040-4039
DOIs	https://doi.org/10.1016/j.tetlet.2014.08.119
Publication status	Published - 2014

Keywords

Aromatic oligoamides
Automated synthesis
Microwave-assisted synthesis
Solid-phase synthesis
Submonomer synthesis

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10.1016/j.tetlet.2014.08.119

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title = "Rapid and convenient semi-automated microwave-assisted solid-phase synthesis of arylopeptoids",

abstract = "A facile and expedient route to the synthesis of arylopeptoid oligomers (N-alkylated aminomethyl benz-amides) using semi-automated microwave-assisted solid-phase synthesis is presented. The synthesis was optimized for the incorporation of side chains derived from sterically hindered or unreactive amines and both ortho- and para-substituted arylo-backbones. By utilizing this optimized protocol a complex nonameric arylopeptoid was synthesized in less than 11 h, featuring a novel alternating ortho-, meta-, and para-substituted backbone pattern and a variety of chemically diverse and challenging side chains.",

keywords = "Aromatic oligoamides, Automated synthesis, Microwave-assisted synthesis, Solid-phase synthesis, Submonomer synthesis",

author = "Rasmussen, {Jakob Ewald} and Boccia, {Marcello Massimo} and John Nielsen and Claude Taillefumier and Sophie Faure and Thomas Hjelmgaard",

year = "2014",

doi = "10.1016/j.tetlet.2014.08.119",

language = "English",

volume = "55",

pages = "5940--5943",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Pergamon Press",

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TY - JOUR

T1 - Rapid and convenient semi-automated microwave-assisted solid-phase synthesis of arylopeptoids

AU - Rasmussen, Jakob Ewald

AU - Boccia, Marcello Massimo

AU - Nielsen, John

AU - Taillefumier, Claude

AU - Faure, Sophie

AU - Hjelmgaard, Thomas

PY - 2014

Y1 - 2014

N2 - A facile and expedient route to the synthesis of arylopeptoid oligomers (N-alkylated aminomethyl benz-amides) using semi-automated microwave-assisted solid-phase synthesis is presented. The synthesis was optimized for the incorporation of side chains derived from sterically hindered or unreactive amines and both ortho- and para-substituted arylo-backbones. By utilizing this optimized protocol a complex nonameric arylopeptoid was synthesized in less than 11 h, featuring a novel alternating ortho-, meta-, and para-substituted backbone pattern and a variety of chemically diverse and challenging side chains.

AB - A facile and expedient route to the synthesis of arylopeptoid oligomers (N-alkylated aminomethyl benz-amides) using semi-automated microwave-assisted solid-phase synthesis is presented. The synthesis was optimized for the incorporation of side chains derived from sterically hindered or unreactive amines and both ortho- and para-substituted arylo-backbones. By utilizing this optimized protocol a complex nonameric arylopeptoid was synthesized in less than 11 h, featuring a novel alternating ortho-, meta-, and para-substituted backbone pattern and a variety of chemically diverse and challenging side chains.

KW - Aromatic oligoamides

KW - Automated synthesis

KW - Microwave-assisted synthesis

KW - Solid-phase synthesis

KW - Submonomer synthesis

U2 - 10.1016/j.tetlet.2014.08.119

DO - 10.1016/j.tetlet.2014.08.119

M3 - Journal article

AN - SCOPUS:84907584839

SN - 0040-4039

VL - 55

SP - 5940

EP - 5943

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Rapid and convenient semi-automated microwave-assisted solid-phase synthesis of arylopeptoids

Abstract

Keywords

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