Mechanochemical Synthesis of Primary Amides

Gómez-Carpintero, Jorge; Sánchez, Juan Domingo; González, Juan Francisco; Menéndez, J. Carlos

doi:10.1021/acs.joc.1c02350

Cited by 26 publications

(21 citation statements)

References 51 publications

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“…Isidro-Llobet et al published a comprehensive review discussing the sustainability of peptide synthesis in scale-up methods (73). They presented novel green industrial methods, including peptide synthesis in flow (74,75), greener tag-assisted liquid phase peptide synthesis (76,77), nanofiltration (78), membrane-enhanced peptide synthesis (79,80), enzymatic peptide synthesis (81,82), and mechanochemistry (83,84). Moreover, Martin et al thoroughly reviewed the green approaches for SPPS (85).…”

Section: Sustainable Methodsmentioning

confidence: 99%

Chemical Wastes in the Peptide Synthesis Process and Ways to Reduce Them

et al. 2022

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: In recent decades, a growing interest has been observed among pharmaceutical companies in producing and selling 80 FDA-approved therapeutic peptides. However, there are many drawbacks to peptide synthesis at the academic and industrial scales, involving the use of large amounts of highly hazardous coupling reagents and solvents. This review focuses on hideous and observant wastes produced before, during, and after peptide synthesis and proposes some solutions to reduce them.

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Section: Sustainable Methodsmentioning

confidence: 99%

Chemical Wastes in the Peptide Synthesis Process and Ways to Reduce Them

et al. 2022

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“…In the context of nitrogen generation capable of reacting with organic compounds, Menéndez and co-workers also contributed with a swift and easy reaction via ball mill. [131] When calcium nitride is ball milled with an ester, under the mild conditions reported in Scheme 20, it afforded the corresponding amide product in good to high yields. The group made a broad scope of aromatics, heteroaromatics and amino acid compounds, demonstrating the technique's potential.…”

Section: Mechanochemical Processes Developed In the Presence Of (Soli...mentioning

confidence: 99%

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

et al. 2022

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Mechanochemical transformations have made chemists enter unknown territories, forcing a different chemistry perspective. While questioning or revisiting familiar concepts belonging to solution chemistry, mechanochemistry has broken new ground, especially in the panorama of organic synthesis. Not only does it foster new "thinking outside the box", but it also has opened new reaction paths, allowing to overcome the weaknesses of traditional chemistry exactly where the use of well-established solution-based methodologies rules out progress. In this Review, the reader is introduced to an intriguing research subject not yet fully explored and waiting for improved understanding. Indeed, the study is mainly focused on organic transformations that, although impossible in solution, become possible under mechanochemical processing conditions, simultaneously entailing innovation and expanding the chemical space.This publication is part of a joint Special Collection of Chemistry-Methods and ChemSusChem including invited contributions focusing on "Methods and Applications in Mechanochemistry". Please visit chemsuschem.org/ collections to view all contributions.

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“…This approach was used efficiently in the synthesis of rufinamide, an anti‐epileptic compound (Scheme 4). [34] Access to triazole‐ester precursor 1 was performed according to literature procedures in solution but using water as solvent, through an azide formation following by a 3+2 Huisgen cycloaddition reaction. Finally, 1 was converted into rufinamide by grinding the ethyl ester with Ca 3 N 2 and a catalytic quantity of indium(III) chloride as Lewis acid.…”

Section: Mechanosynthesis Of Biologically Active Heterocyclic Compoundsmentioning

confidence: 99%

Sustainable Mechanosynthesis of Biologically Active Molecules

et al. 2022

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Synthetic mechanochemistry, the use of mechanical force produced by milling, grinding or extruding, as an activation technique, provides access to chemical entities of all kinds. This Review is focused on examples reported so far of known Active Pharmaceutical Ingredients (APIs), and effectively evaluated bioactive molecules, all prepared by mechanosynthesis. Three families of molecules are discussed: heterocyclic compounds, metal complexes and peptides. Advantages of the mechanochemistry approach are highlighted especially from a green chemistry and efficacy point of view.

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Mechanochemical Synthesis of Primary Amides

Cited by 26 publications

References 51 publications

Chemical Wastes in the Peptide Synthesis Process and Ways to Reduce Them

Chemical Wastes in the Peptide Synthesis Process and Ways to Reduce Them

Mechanochemistry: New Tools to Navigate the Uncharted Territory of “Impossible” Reactions

Sustainable Mechanosynthesis of Biologically Active Molecules

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