1004997-26-5Relevant articles and documents
Highly efficient method for the synthesis of carboxamides from carboxylic acids and amines using pyridine-3-sulfonyl chloride (3-PSC)
Funasaka, Setsuo,Kato, Koji,Mukaiyama, Teruaki
, p. 506 - 507 (2008)
The use of pyridine-3-sulfonyl chloride (3-PSC) in dehydrating condensation was investigated. This novel reagent was successfully employed as a mild dehydrating reagent for preparing various carboxamides in good to excellent yields from the corresponding carboxylic acids and amines. Copyright
Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis
Lee, Hyo-Jun,Huang, Xiao,Sakaki, Shigeyoshi,Maruoka, Keiji
, p. 848 - 855 (2021/02/09)
A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.
A versatile biosynthetic approach to amide bond formation
Philpott, Helena K.,Thomas, Pamela J.,Tew, David,Fuerst, Doug E.,Lovelock, Sarah L.
supporting information, p. 3426 - 3431 (2018/08/07)
The development of versatile and sustainable catalytic strategies for amide bond formation is a major objective for the pharmaceutical sector and the wider chemical industry. Herein, we report a biocatalytic approach to amide synthesis which exploits the diversity of Nature's amide bond forming enzymes, N-acyltransferases (NATs) and CoA ligases (CLs). By selecting combinations of NATs and CLs with desired substrate profiles, non-natural biocatalytic pathways can be built in a predictable fashion to allow access to structurally diverse secondary and tertiary amides in high yield using stoichiometric ratios of carboxylic acid and amine coupling partners. Transformations can be performed in vitro using isolated enzymes, or in vivo where reactions rely solely on cofactors generated by the cell. The utility of these whole cell systems is showcased through the preparative scale synthesis of a key intermediate of Losmapimod (GW856553X), a selective p38-mitogen activated protein kinase inhibitor.
Efficient synthesis of new N-benzyl- or N-(2-furylmethyl)cinnamamides promoted by the 'green' catalyst boric acid, and their spectral analysis
Barajas, Jose Gregorio Hernandez,Mendez, Leonor Yamile Vargas,Kouznetsov, Vladimir V.,Stashenko, Elena E.
, p. 377 - 382 (2008/09/20)
New N-benzyl- or N-(2-furylmethyl)cinnamamides were prepared in good to excellent yields by amidation reactions between cinnamic acid and benzylamines or (2-furylmethyl)amine in the presence of 5 mol% boric acid. All the cinnamamides were characterized by IR and 1H and 13C NMR spectroscopy. Georg Thieme Verlag Stuttgart.
Oxidation of aliphatic α,β-unsaturated aldimines to amides specifically by oxone with AlCl3
Lu, Zhou,Peng, Lijun,Wu, Wentao,Wu, Longmin
, p. 2357 - 2366 (2008/09/21)
α,β-Unsaturated aldimines were specifically oxidized to amides with Oxone in the presence of AlCl3 as a Lewis acid in CH2Cl2. No migration of aryl group occurred in the rearrangement reaction. Copyright Taylor & Francis Group, LLC.
Highly efficient method for the synthesis of carboxamides from carboxylic acids and amines using benzenesulfonic anhydride (BSA)
Funasaka, Setsuo,Kato, Koji,Mukaiyama, Teruaki
, p. 1456 - 1457 (2008/03/14)
A highly efficient method by using benzenesulfonic anhydride (BSA) in the presence of 4-(dimethylamino)pyridine (DMAP) to synthesize carboxamides from various carboxylic acids and amines including sterically hindered ones is established. This reaction proceeds smoothly to provide the desired product in high yield. Copyright
