{"title":"Condensation of carboxylic acids with amines using the Boc<sub>2</sub>O/DMAP system under solvent-free conditions.","authors":"Mourad Boukachabia, Mounia Merabet-Khelassi, Olivier Riant","doi":"10.1039/d4ob01868k","DOIUrl":null,"url":null,"abstract":"<p><p>The present study describes the use of the di-<i>tert</i>-butyl dicarbonate (Boc<sub>2</sub>O)/4-(<i>N</i>,<i>N</i>-dimethylamino)pyridine (DMAP) system for the amidation of carboxylic acids under neat conditions without heating. A set of carboxylic acids was explored, such as non-steroidal anti-inflammatory drugs (NSAIDs), fatty acids and protected prolines in the presence of aromatic, benzylic and aliphatic amines as nucleophilic partners. The scope of this easy approach was extended to the preparation of thirty-two diverse carboxylic amides, which were recovered with isolated yields varying from moderate to excellent. To increase the value of this protocol, a scalable chemoselective amidation of oleic acid with ethanolamine was successfully established. The corresponding fatty carboxylic amide, <i>N</i>-oleoylethanolamide (OEA), was recovered with 73% yield. This study highlights the potency of the use of mixed anhydrides formed <i>in situ</i> and the pursuit of the reaction profile reveals sequential steps rather than a one-pot process.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4ob01868k","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The present study describes the use of the di-tert-butyl dicarbonate (Boc2O)/4-(N,N-dimethylamino)pyridine (DMAP) system for the amidation of carboxylic acids under neat conditions without heating. A set of carboxylic acids was explored, such as non-steroidal anti-inflammatory drugs (NSAIDs), fatty acids and protected prolines in the presence of aromatic, benzylic and aliphatic amines as nucleophilic partners. The scope of this easy approach was extended to the preparation of thirty-two diverse carboxylic amides, which were recovered with isolated yields varying from moderate to excellent. To increase the value of this protocol, a scalable chemoselective amidation of oleic acid with ethanolamine was successfully established. The corresponding fatty carboxylic amide, N-oleoylethanolamide (OEA), was recovered with 73% yield. This study highlights the potency of the use of mixed anhydrides formed in situ and the pursuit of the reaction profile reveals sequential steps rather than a one-pot process.
期刊介绍：
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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