Coupling biocatalysis with high-energy flow reactions for the synthesis of carbamates and β-amino acid derivatives

    • Alexander Leslie1
    • Thomas S. Moody2,3
    • Megan Smyth2
    • Scott Wharry2
    • Marcus Baumann1
    • 1School of Chemistry, University College Dublin, D04 N2E2, Ireland
    • 2Almac Group Ltd., Craigavon BT63 5QD, United Kingdom
    • 3Arran Chemical Company, Athlone, Co. Roscommon N37 DN24, Ireland

    A continuous flow process is presented that couples a Curtius rearrangement step with a biocatalytic impurity tagging strategy to produce a series of valuable Cbz-carbamate products. Immobilized CALB was exploited as a robust hydrolase to transform residual benzyl alcohol into easily separable benzyl butyrate. The resulting telescoped flow process was effectively applied across a series of acid substrates rendering the desired carbamate structures in high yield and purity. The derivatization of these products via complementary flow-based Michael addition reactions furthermore demonstrated the creation of β-amino acid species. This strategy thus highlights the applicability of this work towards the creation of important chemical building blocks for the pharmaceutical and speciality chemical industries.

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