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Cobalt-catalyzed carbonylation of phenylacetaldehyde to N-acetyl-beta-phenylalanine

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Abstract

N-acetyl-beta-phenylalanine has been produced by the reaction of phenylacetaldehyde, acetamide and CO/H2 in the presence of cobalt carbonyl catalyst. N- acetyl-beta-phenylalanine yields of 72-82 mol% and cobalt recoveries of 98% had been achieved under the conditions of 2000 psi of 3 : 1 CO/H2 and 80°C in a batch process. The presence of a suitable ligand, 1,2-bis(diphenylphosphino)ethane, was essential for maintaining cobalt in homogeneous solution. The feasibility of using a continuous phase reactor with a dual feed stream system was demonstrated. N-acetyl-beta-phenylalanine is proposed to be the precursor to L-phenylalanine, the key intermediate for aspartame sweetener.

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Authors
  1. J.-J. Lin
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  2. J.F. Knifton
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Lin, JJ., Knifton, J. Cobalt-catalyzed carbonylation of phenylacetaldehyde to N-acetyl-beta-phenylalanine. Catalysis Letters 45, 139–141 (1997). https://doi.org/10.1023/A:1019042907241

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  • DOI: https://doi.org/10.1023/A:1019042907241

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