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Primary Amine–Promoted Ring Opening in Carbapenem-derived p-Nitrobenzyl Esters

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Abstract

Ethylamine and ethanolamine react with 4-nitrobenzyl (4R,5S,6S)-3-[(2-furylmethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, leading to the opening of the β-lactam ring by C7–N bond cleavage accompanied and simultaneous amidation of the ester groups. In this anionoid transformation, the enamine–imine rearrangement followed by stereoselective protonation provides the formation of enantiomerically pure pyrrolidine derivatives: (2S,3R,4S)-N-ethyl-2-{(1S,2R)-1-[(ethylamino)-carbonyl]-2-hydroxypropyl}-4-[(2-furylmethyl)sulfanyl]-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxamide and (2S,3R,4S)-4-[(2-furylmethyl)sulfanyl]-N-(2-hydroxyethyl)-2-[(1S,2R)-2-hydroxy-{[(2-hydroxyethyl)-amino]-carbonyl}propyl]-3-methyl-3,4-dihydro-2H-pyrrole-5-carboxamide.

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ACKNOWLEDGMENTS

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

Funding

The work was financially supported by the Russian Science Foundation (project no. 15-13-00039-P).

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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, А. М. Galeeva, А. N. Lobov & М. S. Miftakhov

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  1. Z. R. Valiullina
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  2. А. М. Galeeva
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  3. А. N. Lobov
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  4. М. S. Miftakhov
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Correspondence to Z. R. Valiullina.

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Valiullina, Z.R., Galeeva, А.М., Lobov, А.N. et al. Primary Amine–Promoted Ring Opening in Carbapenem-derived p-Nitrobenzyl Esters. Russ J Org Chem 56, 287–291 (2020). https://doi.org/10.1134/S1070428020020189

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