Development of a Continuously Operating Process for the Enantioselective Synthesis of a beta-Amino Acid Ester via a Solvent-Free Chemoenzymatic Reaction Sequence

Strompen S, Weiss M, Gröger H, Hilterhaus L, Liese A (2013)
Advanced Synthesis & Catalysis 355(11-12): 2391-2399.

Journal Article | Published | English

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Abstract
A sequential, chemoenzymatic process for a continuously operating production of the chiral -amino acid ester ethyl (S)-3-(benzylamino)butanoate was developed. The reactor set-up combined a plug-flow reactor for the thermal aza-Michael addition of benzylamine to trans-ethyl crotonate coupled to a subsequent packed-bed reactor for the lipase (Novozym 435)-catalyzed kinetic resolution of the racemic intermediate product, which was formed in the initial step. The coupled reactors were operated continuously for a time period of 4 days without significant loss of enzyme activity. The target -amino acid ester was obtained with 92% conversion in the plug-flow reactor and 59% conversion in the packed bed reactor at high enantiomeric excess of >98%. A space-time yield of 0.4kgL(-1)d(-1) was calculated for the total reactor system and 1.8kgL(-1)d(-1) based solely on the volume of the packed bed reactor. A total turnover number of 158,000 was calculated for the biocatalyst assuming the same deactivation rate as observed in batch experiments. The continuously operating, solvent-free process thus represents an efficient method for the enantioselective production of a value added (S)âamino acid ester starting from cheap substrates.
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Strompen S, Weiss M, Gröger H, Hilterhaus L, Liese A. Development of a Continuously Operating Process for the Enantioselective Synthesis of a beta-Amino Acid Ester via a Solvent-Free Chemoenzymatic Reaction Sequence. Advanced Synthesis & Catalysis. 2013;355(11-12):2391-2399.
Strompen, S., Weiss, M., Gröger, H., Hilterhaus, L., & Liese, A. (2013). Development of a Continuously Operating Process for the Enantioselective Synthesis of a beta-Amino Acid Ester via a Solvent-Free Chemoenzymatic Reaction Sequence. Advanced Synthesis & Catalysis, 355(11-12), 2391-2399.
Strompen, S., Weiss, M., Gröger, H., Hilterhaus, L., and Liese, A. (2013). Development of a Continuously Operating Process for the Enantioselective Synthesis of a beta-Amino Acid Ester via a Solvent-Free Chemoenzymatic Reaction Sequence. Advanced Synthesis & Catalysis 355, 2391-2399.
Strompen, S., et al., 2013. Development of a Continuously Operating Process for the Enantioselective Synthesis of a beta-Amino Acid Ester via a Solvent-Free Chemoenzymatic Reaction Sequence. Advanced Synthesis & Catalysis, 355(11-12), p 2391-2399.
S. Strompen, et al., “Development of a Continuously Operating Process for the Enantioselective Synthesis of a beta-Amino Acid Ester via a Solvent-Free Chemoenzymatic Reaction Sequence”, Advanced Synthesis & Catalysis, vol. 355, 2013, pp. 2391-2399.
Strompen, S., Weiss, M., Gröger, H., Hilterhaus, L., Liese, A.: Development of a Continuously Operating Process for the Enantioselective Synthesis of a beta-Amino Acid Ester via a Solvent-Free Chemoenzymatic Reaction Sequence. Advanced Synthesis & Catalysis. 355, 2391-2399 (2013).
Strompen, Simon, Weiss, Markus, Gröger, Harald, Hilterhaus, Lutz, and Liese, Andreas. “Development of a Continuously Operating Process for the Enantioselective Synthesis of a beta-Amino Acid Ester via a Solvent-Free Chemoenzymatic Reaction Sequence”. Advanced Synthesis & Catalysis 355.11-12 (2013): 2391-2399.
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