Issue 39, 2013
From the journal:

Organic & Biomolecular Chemistry

A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitorAtazanavir

Luciana Dalla-Vechia,a   Benedikt Reichart,b   Toma Glasnov,b   Leandro S. M. Miranda,a   C. Oliver Kappe*bc  and  Rodrigo O. M. A. de Souza*a  

* Corresponding authors

a Biocatalysis and Organic Synthesis Group, Chemistry Institute, Federal University of Rio de Janeiro, CEP 22941 909, Rio de Janeiro, Brazil
E-mail: rodrigosouza@iq.ufrj.br
Fax: (+55)-212-5627001

b Christian Doppler Laboratory for Microwave Chemistry (CDLMC) and Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz, Austria
E-mail: oliver.kappe@uni-graz.at
Fax: (+43)-316-3809840
Tel: (+43)-316-3805352

c Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia

Abstract

The development of multistep continuous flow reactions for the synthesis of important intermediates for the pharmaceutical industry is still a significant challenge. In the present contribution the biaryl-hydrazine unit of Atazanavir, an important HIV protease inhibitor, was prepared in a three-step continuous flow sequence in 74% overall yield. The synthesis involved Pd-catalyzed Suzuki–Miyaura cross-coupling, followed by hydrazone formation and a subsequent hydrogenation step, and additionally incorporates a liquid–liquid extraction step.

Graphical abstract: A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitorAtazanavir

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Article information

DOI
https://doi.org/10.1039/C3OB41464G
Article type
Paper
Submitted
16 Jul 2013
Accepted
12 Aug 2013
First published
14 Aug 2013
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2013,11, 6806-6813

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A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitorAtazanavir

L. Dalla-Vechia, B. Reichart, T. Glasnov, L. S. M. Miranda, C. O. Kappe and R. O. M. A. de Souza, Org. Biomol. Chem., 2013, 11, 6806 DOI: 10.1039/C3OB41464G

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