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Synthesis of a C3 Hydroxyproline-modified Carbapenem

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Abstract

Methyl (4R)-4-hydroxy-1-(sulfanylacetyl)-l-prolinate was synthesized starting from trans-4-l-hydroxyprolinate methyl ester hydrochloride and then reacted with the known carbapenem enol phosphate to obtain the corresponding carbapenem and then to chemically more stable methyl ester.

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ACKNOWLEDGMENTS

Analyses were performed on the equipment of the Khimiya Center for Collective Use, Ufa Institute of Chemistry, Russian Academy of Sciences.

Funding

The work was performed under the state order, topic “Design and Synthesis of Bioactive Natural and Non-natural Cyclopentanoides, Heterocycles, Epothilones and Analogs” (no. 122031400261-4).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    Z. R. Valiullina, A. M. Galeeva & M. S. Miftakhov

Authors
  1. Z. R. Valiullina
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  2. A. M. Galeeva
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  3. M. S. Miftakhov
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Correspondence to Z. R. Valiullina.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 11, pp. 1248–1252 https://doi.org/10.31857/S0514749222110167.

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Valiullina, Z.R., Galeeva, A.M. & Miftakhov, M.S. Synthesis of a C3 Hydroxyproline-modified Carbapenem. Russ J Org Chem 58, 1664–1667 (2022). https://doi.org/10.1134/S1070428022110173

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  • DOI: https://doi.org/10.1134/S1070428022110173

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