Scale-Up of Flow-Assisted Synthesis
of C2-Symmetric Chiral PyBox
Ligands

Claudio Battilocchio; Marcus Baumann; Ian R. Baxendale; Mariangela Biava; Matthew O. Kitching; Steven V. Ley; Rainer E. Martin; Stephan A. Ohnmacht; Nicholas D. C. Tappin

doi:10.1055/s-0031-1289676

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Synthesis 2012(4): 635-647
DOI: 10.1055/s-0031-1289676

PAPER

Scale-Up of Flow-Assisted Synthesis of C ₂-Symmetric Chiral PyBox Ligands

Claudio Battilocchio^a,c, Marcus Baumann^a, Ian R. Baxendale^a, Mariangela Biava^c, Matthew O. Kitching^a, Steven V. Ley^a, Rainer E. Martin*^b, Stephan A. Ohnmacht^b, Nicholas D. C. Tappin^a
^a Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
e-Mail: theitc@ch.cam.ac.uk;
^b F. Hoffmann-La Roche Ltd., Pharmaceuticals Division, Chemistry Technology and Innovation, 4070 Basel, Switzerland
^c Department of Pharmaceutical Chemistry and Technology, Sapienza University of Rome, Rome, Italy

Further Information

Publication History

Received 19 November 2011
Publication Date:
25 January 2012 (online)

Abstract
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Abstract

A series of PyBox ligands were prepared from commercially available chelidonic acid by a multistep flow sequence using mesoreactor technology. A chloro group introduced onto the ligand scaffold was subsequently exploited to give amine derivatives ready for immobilization through microencapsulation technologies.

Key words

ligands - macrocycles - flow chemistry - solid-supported reagent - asymmetric synthesis - scale up

References

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