Chapter 5. Protease-Catalyzed Preparation of (S)-2-[(tert-Butylsulfonyl)-methyl]-hydrocinnamic Acid for Renin Inhibitor RO0425892

  1. Dr. Hans-Ulrich Blaser3,
  2. Dr. Elke Schmidt4
  1. Beat Wirz1,
  2. Stephan Doswald1,
  3. Ernst Kupfer1,
  4. Wolfgang Wostl1,
  5. Thomas Weisbrod2,
  6. Heinrich Estermann1

Published Online: 13 JAN 2004

DOI: 10.1002/3527602151.ch22

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., Doswald, S., Kupfer, E., Wostl, W., Weisbrod, T. and Estermann, H. (2004) Protease-Catalyzed Preparation of (S)-2-[(tert-Butylsulfonyl)-methyl]-hydrocinnamic Acid for Renin Inhibitor RO0425892, 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.ch22

Editor Information

  1. 3

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

  2. 4

    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

    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:

  • (s)-2-[(tert-butylsulfonyl)methyl]hydrocinnamic acid;
  • renin inhibitor RO0425892;
  • synthesis;
  • ethyl sulfopropionate 2;
  • Subtilisin Carlsberg

Summary

This chapter contains sections titled:

  • Introduction

  • The Process Research Synthesis

    • The Synthetic Concept

    • Alternative Concepts

    • Enzymatic Approaches

      • Racemic Resolution of Ethyl Sulfopropionate 2 with α-Chymotrypsin

      • Aminolysis of Ethyl Sulfopropionate 2 with Histidine Methylester 4

  • Enzymatic Resolution of Ethyl Sulfopropionate 2 with Subtilisin Carlsberg

    • Process Research

      • Enzyme Screening

      • Parameter Optimization

      • Work-up

    • Process Development

      • Process Parameters

      • Improved Enzyme Preparation

      • Work-up

    • Pilot Production

      • Equipment

      • Enzyme Reaction

      • Work-up

  • Discussion

  • Acknowlegements

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