Chapter 7. An Innovative Asymmetric Sulfide Oxidation: The Process Development History behind the New Antiulcer Agent Esomeprazole†

  1. Dr. Hans-Ulrich Blaser2,
  2. Dr. Elke Schmidt3
  1. Hans-Jürgen Federsel,
  2. Magnus Larsson

Published Online: 13 JAN 2004

DOI: 10.1002/3527602151.ch24

Book Title

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Additional Information

How to Cite

Federsel, H.-J. and Larsson, M. (2004) An Innovative Asymmetric Sulfide Oxidation: The Process Development History behind the New Antiulcer Agent Esomeprazole, in Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions (eds H.-U. Blaser and E. Schmidt), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527602151.ch24

Editor Information

  1. 2

    Solvias AG, P.O. Box, CH-4002 Basel, Switzerland

  2. 3

    Syngenta Crop Protection AG, CH-4058 Basel, Switzerland

Author Information

  1. Astra Zeneca, Process R&D, S-15185 Södertalje, Sweden

  1. †

    Partly presented in lecture format (orally) at the following conferences and symposia: ChiraSource 2000 in Lisbon, Portugal, October 2–4, 2000; Chiral Europe 2000 in Malta, October 26–27, 2000; 18th SCI Process Development Symposium, Cambridge, UK, December 11–13, 2000; ACS ProSpectives Conference Process Chemistry in the Pharamaceutical Industry, Barcelona, Spain, February 24–27, 2002; 14th International Symposium on Chirality, Hamburg, Germany, September 8–12, 2002.

Publication History

  1. Published Online: 13 JAN 2004
  2. Published Print: 6 NOV 2003

ISBN Information

Print ISBN: 9783527306312

Online ISBN: 9783527602155

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CHAPTER TOOLS

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Keywords:

  • esomeprazole;
  • base;
  • solvent;
  • titanium complex;
  • synthesis;
  • diethyl tartrate;
  • Hünigs base;
  • cumene hydroperoxide;
  • catalytic complex

Summary

This chapter contains sections titled:

  • Major Events at a Glance: An Overview of Achievements from 1979 - 2000

  • Introduction: Omeprazole (Losec(R)) as the Starting Point for a Challenging Project

  • Early Attempts: Turning Unfavorable Odds into Success at Last

  • The Way Forward: Options and Development Strategies

  • The Breakthrough: What a Difference a Day Made!

    • The Base

    • The Solvent

    • The Chiral Auxiliary

    • The Amount of H2O

    • The Effect of Oxidation Time

  • Going from a Bench-scale Synthesis to a Fully Fledged Process

    • Solvent

    • Base

    • Composition of Titanium Complex

    • Equilibration of Titanium Complex

    • Equivalents of Ti-Complex

    • Layout of Synthesis

  • The Big Test: Going to Plant Scale

  • Reaching the Final Target: A Robust Commercial Process

    • Water

    • Diethyl Tartrate

    • Hünigs Base

    • Cumene Hydroperoxide

    • Stability of the Catalytic Complex

    • Reaching the Goal – A Robust Process

  • Points to Learn and Conclusions

  • Acknowledgements

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