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Synthesis and enantioselective lipase-catalyzed kinetic resolution of methyl 6-(methoxycarbonyl-methyl)sulfanyl-1,4-dihydropyridine-3-carboxylates

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Chemistry of Heterocyclic Compounds Aims and scope

A series of methyl 6-(methoxycarbonylmethyl)sulfanyl-1,4-dihydropyridine-3-carboxylates as more lipophilic derivatives of biologically active 6-methylsulfanyl-1,4-dihydropyridine-3-carboxylic acid esters has been prepared by alkylation of 6-thioxo-1,4-dihydropyridines with methyl bromoacetate. The kinetic resolution catalyzed by Candida antarctica lipase B (Novozym 435®) has been investigated; the enantiomeric excess of the target products reached 70%. The experiments revealed that the 6-(methoxycarbonylmethyl)sulfanyl group is an essentially new activating group, which, being removed by five bonds from the chiral center, undergoes easy enzymatic hydrolysis and could be used for kinetic resolution of racemic 1,4-dihydropyridines.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, 21 Aizkraukles St., Riga, LV-1006, Latvia

    Z. Andzans, A. Krauze, I. Adlere, L. Krasnova & G. Duburs

  2. The University of Latvia, 19 Raina Blvd., Riga, LV-1586, Latvia

    Z. Andzans

Authors
  1. Z. Andzans
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  2. A. Krauze
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  3. I. Adlere
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  4. L. Krasnova
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  5. G. Duburs
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Correspondence to Z. Andzans.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 454-460, March, 2013.

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Andzans, Z., Krauze, A., Adlere, I. et al. Synthesis and enantioselective lipase-catalyzed kinetic resolution of methyl 6-(methoxycarbonyl-methyl)sulfanyl-1,4-dihydropyridine-3-carboxylates. Chem Heterocycl Comp 49, 421–427 (2013). https://doi.org/10.1007/s10593-013-1263-8

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  • DOI: https://doi.org/10.1007/s10593-013-1263-8

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