Separation of racemic bicalutamide by an optimized combination of continuous 
chromatography and selective crystallization

Kaemmerer, H.; Horvath, Z.; Lee, J. W.; Kaspereit, M.; Arnell, R.; Hedberg, M. H.; Herschend, B.; Jones, M. J.; Larson, K.; Lorenz, H.; Seidel-Morgenstern, A.

doi:10.1021/op200136z

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Separation of racemic bicalutamide by an optimized combination of continuous chromatography and selective crystallization

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Kaemmerer, H.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;
Evonik Industries AG, Hanau, Germany;

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Horvath, Z.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

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Lee, J. W.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

/persons/resource/persons86349

Kaspereit, M.
Process Synthesis and Process Dynamics, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

/persons/resource/persons86390

Lorenz, H.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

/persons/resource/persons86477

Seidel-Morgenstern, A.
Physical and Chemical Foundations of Process Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;
Otto-von-Guericke-Universität Magdeburg, External Organizations;

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Citation

Kaemmerer, H., Horvath, Z., Lee, J. W., Kaspereit, M., Arnell, R., Hedberg, M. H., et al. (2012). Separation of racemic bicalutamide by an optimized combination of continuous chromatography and selective crystallization. Organic Process Research & Development, 16(2), 331-342. doi:10.1021/op200136z.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0013-89CF-F

Abstract

A racemic mixture of bicalutamide, a drug substance used in the treatment of prostate cancer, was separated by simulated moving bed chromatography with the objective of maximizing throughput at reduced outlet purity. The enriched extract stream was purified further by a crystallization process exploiting a shift in the eutectic composition. The optimal purity in between both process steps was identified. The separation scheme developed was validated on a scale of 600 g and the results were compared to the state-of-the art and discussed. The investigated scheme revealed a wide range of promising coupling conditions while showing superior productivities and enhanced process robustness. Copyright © 2011 American Chemical Society [accessed October 7th 2011]