title: Continuous flow synthesis and scale-up of glycine- and taurine-conjugated bile salts.
abstract: A multi-gram scale protocol for the N-acyl amidation of bile acids with glycine and taurine has been successfully developed under continuous flow processing conditions. Selecting ursodeoxycholic acid (UDCA) as the model compound and N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ) as the condensing agent, a modular mesoreactor assisted flow set-up was employed to significantly speed up the optimization of the reaction conditions and the flow scale-up synthesis. The results in terms of yield, in line purification, analysis, and implemented flow set-up for the reaction optimization and large scale production are reported and discussed.
authors.affiliation: Dipartimento di Chimica e Tecnologia del Farmaco, Università di Perugia, Via del Liceo, 1, 06123 Perugia, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Venturoni
authors.forename: Antimo
authors.initials: A
authors.lastname: Gioiello
authors.forename: Roccaldo
authors.initials: R
authors.lastname: Sardella
authors.forename: Benedetto
authors.initials: B
authors.lastname: Natalini
authors.forename: Roberto
authors.initials: R
authors.lastname: Pellicciari
mesh_terms: D000586:Amination; D001647:Bile Acids and Salts / Q000737:chemistry*; D005998:Glycine / Q000138:chemical synthesis*; D006801:Humans; D015394:Molecular Structure; D013654:Taurine / Q000138:chemical synthesis*
chemical_list: D001647:Bile Acids and Salts; D013654:Taurine; D005998:Glycine