Chapter 22. An Efficient, Asymmetric Synthesis of Odanacatib, a Selective Inhibitor of Cathepsin K for the Treatment of Osteoporosis, Using an Enzyme-Mediated Dynamic Kinetic Resolution

  1. Dr. Hans-Ulrich Blaser2 and
  2. Dr. Hans-Jürgen Federsel Director3
  1. Matthew D. Truppo

Published Online: 8 JUN 2010

DOI: 10.1002/9783527630639.ch22

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, Second Edition

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, Second Edition

How to Cite

Truppo, M. D. (2010) An Efficient, Asymmetric Synthesis of Odanacatib, a Selective Inhibitor of Cathepsin K for the Treatment of Osteoporosis, Using an Enzyme-Mediated Dynamic Kinetic Resolution, in Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, Second Edition (eds H.-U. Blaser and H.-J. Federsel), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. doi: 10.1002/9783527630639.ch22

Editor Information

  1. 2

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

  2. 3

    AstraZeneca, 151 85 Södertälje, Sweden

Author Information

  1. Merck & Co., Inc., Department of Process Research, Merck Research Laboratories, Rahway, NJ 07065, USA

Publication History

  1. Published Online: 8 JUN 2010
  2. Published Print: 19 MAY 2010

ISBN Information

Print ISBN: 9783527324897

Online ISBN: 9783527630639

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Keywords:

  • odanacatib;
  • chiral synthesis;
  • enzyme-mediated kinetic resolution;
  • kinetic ring opening;
  • fluoroleucine;
  • azlactone hydrolysis;
  • osteoporosis

Summary

This chapter contains sections titled:

  • Introduction

  • Fluoroleucine Synthesis Strategy

  • First-Generation Enzymatic Dynamic Kinetic Resolution: Batch Process

  • Development of Enzymatic Dynamic Kinetic Resolution: Towards a Manufacturing Process

  • Pilot Plant Runs

  • Conclusion

  • Acknowledgment

  • References