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

被引：31

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

共 27 条

[1] Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?
Brow, Dean G.
Bostrom, Jonas
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) : 4443 - 4458
[2] Controlled Solid Phase Peptide Bond Formation Using N-Carboxyanhydrides and PEG Resins in Water
De Marco, Rossella
Tolomelli, Alessandra
Greco, Arianna
Gentilucci, Luca
[J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (06): : 566 - 569
[3] Large-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals
Dunetz, Joshua R.
Magano, Javier
Weisenburger, Gerald A.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (02) : 140 - 177
[4] ECHA, Candidate list of Substances of Very High Concern for Authorisation
[5] Peptide Coupling Reagents, More than a Letter Soup
El-Faham, Ayman
Albericio, Fernando
[J]. CHEMICAL REVIEWS, 2011, 111 (11) : 6557 - 6602
[6] Amide and Peptide Bond Formation in Water at Room Temperature
Gabriel, Christopher M.
Keener, Megan
Gallou, Fabrice
Lipshutz, Bruce H.
[J]. ORGANIC LETTERS, 2015, 17 (16) : 3968 - 3971
[7] Solid-Phase Peptide Synthesis in Water Using Microwave-Assisted Heating
Galanis, Athanassios S.
Albericio, Fernando
Grotli, Morten
[J]. ORGANIC LETTERS, 2009, 11 (20) : 4488 - 4491
[8] CARBODIIMIDE-MEDIATED AMIDE FORMATION IN A 2-PHASE SYSTEM - A HIGH-YIELD AND LOW-RACEMIZATION PROCEDURE FOR PEPTIDE-SYNTHESIS
HO, GJ
EMERSON, KM
MATHRE, DJ
SHUMAN, RF
GRABOWSKI, EJJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) : 3569 - 3570
[9] Solid phase peptide synthesis in water VI: Evaluation of water-soluble coupling reagents for solid phase peptide synthesis in aqueous media
Hojo, K
Maeda, M
Tanakamaru, N
Mochida, K
Kawasaki, K
[J]. PROTEIN AND PEPTIDE LETTERS, 2006, 13 (02) : 189 - 192
[10] Development of a Method for the Solid-Phase Peptide Synthesis in Water
Hojo, Keiko
Ichikawa, Hideki
Fukumori, Yoshinobu
Kawasaki, Koichi
[J]. INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2008, 14 (04) : 373 - 380

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