Chapter 4. Multi-Kilo Resolution of XU305, a Key Intermediate to the Platelet Glycoprotein IIb/IIIa Receptor Antagonist Roxifiban via Kinetic and Dynamic Enzymatic Resolution

  1. Dr. Hans-Ulrich Blaser3,
  2. Dr. Elke Schmidt4
  1. Jaan A. Pesti1,
  2. Luigi Anzalone2

Published Online: 13 JAN 2004

DOI: 10.1002/3527602151.ch21

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

Pesti, J. A. and Anzalone, L. (2004) Multi-Kilo Resolution of XU305, a Key Intermediate to the Platelet Glycoprotein IIb/IIIa Receptor Antagonist Roxifiban via Kinetic and Dynamic Enzymatic Resolution, 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.ch21

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

    Bristol-Myers Squibb, Process R & D, Pharmaceutical Research Institute, B.O. Box, Princeton, NJ 08543-4000, USA

  2. 2

    Johnson & Johnson, Pharmaceutical Research & Development, LLC, Spring House, PA 19477, USA

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:

  • XU305;
  • roxifiban;
  • enzymatic resolution;
  • scale-up;
  • racemization;
  • thioester 10b

Summary

This chapter contains sections titled:

  • Introduction

  • Scale-up of the Kinetic Enzymatic Resolution of 9 to 1

    • Development of the Resolution of (R,S)-9

    • Racemization of 9

      • Mechanism of Isoxazoline (9) Racemization

  • Process Development of the Dynamic Enzymatic Resolution of Thioester 10b

    • Identification of Efficient Reaction Conditions for Dynamic Enzymatic Resolution

    • Preparation of 1-Propyl Thioester (10b)

    • Scale-up of the Dynamic Enzymatic Resolution Chemistry into the Plant

  • Conclusions

  • Acknowledgements

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