Enabling amidation in water: micellar catalysis approach for sustainable synthesis of iopamidol.

Autor:	Zucchi A; Department of Materials Science, University of Milano Bicocca Via R.Cozzi 55 Milano I-20125 Italy luca.beverina@unimib.it., Mattiello S; Department of Materials Science, University of Milano Bicocca Via R.Cozzi 55 Milano I-20125 Italy luca.beverina@unimib.it., Maschio R; Università del Piemonte Orientale, Dipartimento di Scienze del Farmaco Largo Donegani 2/3 Novara 28100 (NO) Italy., Bellotti V; Department of Materials Science, University of Milano Bicocca Via R.Cozzi 55 Milano I-20125 Italy luca.beverina@unimib.it., Giovenzana GB; Università del Piemonte Orientale, Dipartimento di Scienze del Farmaco Largo Donegani 2/3 Novara 28100 (NO) Italy., Lattuada L; Bracco Imaging S.p.A Via Egidio Folli 50 Milano I-20134 Italy., Beverina L; Department of Materials Science, University of Milano Bicocca Via R.Cozzi 55 Milano I-20125 Italy luca.beverina@unimib.it.
Jazyk:	angličtina
Zdroj:	RSC advances [RSC Adv] 2024 Dec 18; Vol. 14 (54), pp. 39902-39907. Date of Electronic Publication: 2024 Dec 18 (Print Publication: 2024).
DOI:	10.1039/d4ra08529a
Abstrakt:	Micellar catalysis is becoming an increasingly versatile tool to carry out a wide range of organic transformations using water as the reaction medium. The approach was recently found to be effective also in the case of water sensitive organics such as acyl chlorides. This finding is of great relevance for the manufacturing of challenging substrates such as the known iodinated contrast agent iopamidol, requiring the use of aprotic dipolar solvents (DMF, NMP, DMAc) in the key amidation step of an acyl dichloride intermediate with serinol. These solvents are subjected to an increasing regulatory pressure due to safety and environmental concerns. We show that the amidation step can be straightforwardly performed in water containing the industrial surfactant Triton X-100, provided that the employed amine is not water soluble. Accordingly, we developed suitable lipophilic serinol derivatives that, after amidation and hydrolysis, directly gave iopamidol in a one-pot process. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
Externí odkaz:	Zobrazit plný text záznamu