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Issue 20, 2012
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Continuous flow synthesis and scale-up of glycine- and taurine-conjugated bile salts

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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.

Graphical abstract: Continuous flow synthesis and scale-up of glycine- and taurine-conjugated bile salts

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Publication details

The article was received on 12 Mar 2012, accepted on 22 Mar 2012 and first published on 23 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25528F
Citation: Org. Biomol. Chem., 2012,10, 4109-4115
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    Continuous flow synthesis and scale-up of glycine- and taurine-conjugated bile salts

    F. Venturoni, A. Gioiello, R. Sardella, B. Natalini and R. Pellicciari, Org. Biomol. Chem., 2012, 10, 4109
    DOI: 10.1039/C2OB25528F

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