Chapter 6. Protease-Catalyzed Preparation of Chiral 2-Isobutyl Succinic Acid Derivatives for Collagenase Inhibitor RO0319790

  1. Dr. Hans-Ulrich Blaser4,
  2. Dr. Elke Schmidt5
  1. Beat Wirz1,
  2. Milan Soukup2,
  3. Thomas Weisbrod3,
  4. Florian Stäbler1,
  5. Rolf Birk1

Published Online: 13 JAN 2004

DOI: 10.1002/3527602151.ch23

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

Wirz, B., Soukup, M., Weisbrod, T., Stäbler, F. and Birk, R. (2004) Protease-Catalyzed Preparation of Chiral 2-Isobutyl Succinic Acid Derivatives for Collagenase Inhibitor RO0319790, 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.ch23

Editor Information

  1. 4

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

  2. 5

    Syngenta Crop Protection AG, CH-4058 Basel, Switzerland

Author Information

  1. 1

    F. Hoffmann-La Roche Ltd, Grenzacherstrasse 124, Postfach, CH-4070 Basel, Switzerland

  2. 2

    Efeuweg 5, CH-4103 Bottmingen, Switzerland

  3. 3

    European Patent Office, Bayerstr. 35, D-80335 München, Germany

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:

  • 2-isobutyl succinic acid;
  • collagenase inhibitor RO0319790;
  • synthesis;
  • enzymatic resolution;
  • diethyl 2-isobutyl succinate 9;
  • racemization

Summary

This chapter contains sections titled:

  • Introduction

  • The Process Research Synthesis

    • The Synthetic Concept

    • Alternative Concepts

    • Enzymatic Approaches

      • Racemic Resolution of Nitrile Ester 10

      • Enantio- and Regioselective Monohydrolysis of Diester 9

      • Aminolysis in Organic Solvent Systems

      • Coupling of (R)-2a with Amine 13 in Aqueous Milieu

  • Enzymatic Resolution of Diethyl 2-Isobutyl Succinate 9

    • Process Research

      • Selection of the Enzyme

      • Parameter Optimization

      • Substrate Engineering

      • Work-up

      • Racemization of the Antipodal Diester (S)-9

    • Process Development

      • Process Parameters

      • Work-up

      • Racemization

    • Pilot Production

      • Equipment

      • Enzyme Reaction

      • Work-up

  • Discussion

  • Acknowledgments

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