SYNTHESIS AND ENANTIOSELECTIVE LIPASE-CATALYZED KINETIC RESOLUTION OF METHYL 6-(METHOXYCARBONYLMETHYL-SULFANYL)-1,4-DIHYDROPYRIDINE-3-CARBOXYLATES

Authors

  • Z. Andzans Latvian Institute of Organic Synthesis
  • A. Krauze Latvian Institute of Organic Synthesis
  • I. Adlere Latvian Institute of Organic Synthesis
  • L. Krasnova Latvian Institute of Organic Synthesis
  • G. Duburs Latvian Institute of Organic Synthesis

DOI:

https://doi.org/10.1007/124

Abstract

A series of methyl 6-(methoxycarbonylmethyl)sulfanyl-
1,4-dihydropyridine-3-carboxylates 2 as more lipophilic derivatives of biologically active 6-methylthio-1,4-DHP-3-carboxylic acid esters have been prepared by alkylation of 6-thioxo-1,4-dihydropyridines 1 with ethyl omega-bromoalkanoates. Candida Antarctica lipase B (Novozym 435®, CAL-B)-catalyzed kinetic resolution has been investigated. 70% enantiomeric excess was reached for esters 2 in water-saturated IPE at 45 oC. The experiments allowed the characterisation of
6-(methoxycarbonylmethyl)sulfanyl group as an essentially new activating group which being 5 bonds remote from chiral center undergoes easy enzymatic hydrolysis and could be used for kinetic resolution of racemic 1,4-DHPs.

Also published in Chemistry of Heterocyclic Compounds, 2013, 49 (3), pp 421-427

http://link.springer.com/article/10.1007/s10593-013-1263-8

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Published

2013-04-09

Issue

No. 3 (2013)

Section

Original Papers