A comparative study of amide -bond forming reagents in aqueous media - Substrate scope and reagent compatibility

被引：34

作者：

Badland, Matthew ^{[1
]}

Crook, Robert ^{[1
]}

Delayre, Bastien ^{[2
]}

Fussell, Steven J. ^{[1
]}

Gladwell, Lain ^{[1
]}

Hawksworth, Michael ^{[1
]}

Howard, Roger M. ^{[3
]}

Walton, Robert ^{[1
]}

Weisenburger, Gerald A. ^{[3
]}

机构：

[1] Pfizer Worldwide Res & Dev, Discovery Pk, Sandwich CT13 9NJ, Kent, England

[2] CPE Lyon, 43 Bd 11 Novembre 1918, F-69100 Villeurbanne, France

[3] Pfizer Worldwide Res & Dev, Eastern Point Rd, Groton, CT 06340 USA

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 46期

关键词：

Amide-bond forming; Condensation in water; Coupling reagents; PHASE PEPTIDE-SYNTHESIS; COUPLING REAGENTS; CARBOXYLIC-ACIDS; LARGE-SCALE; DMT-MM; WATER; CARBODIIMIDE; AMIDATION; AGENT;

D O I：

10.1016/j.tetlet.2017.10.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A survey of amidation reagents demonstrating DIC-HOPO, DMT-MM, COMU-collidine, TPTU-NMI, EEDQ, CDI and EDC-Oxyma to be effective for the coupling of carboxylic acids with amines in the presence of water and the absence of problematic dipolar aprotic solvents is reported. DMT-MM was shown to provide the best yields for the coupling of a secondary amine, TPTU-NMI and COMU-collidine for aniline, whilst the combination of DIC with HOPO afforded the broadest substrate scope and the highest yields for a sterically demanding carboxylic acid. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：4391 / 4394

页数：4

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