2,2,2-Trifluoroethyl Chlorooxoacetate--Universal Reagent for One-Pot Parallel Synthesis of N(1)-Aryl-N(2)-alkyl-Substituted Oxamides

Andrey V Bogolubsky; Yurii S Moroz; Pavel K Mykhailiuk; Sergey E Pipko; Anton V Zhemera; Anzhelika I Konovets; Olena O Stepaniuk; Inna S Myronchuk; Yurii V Dmytriv; Roman A Doroschuk; Olga A Zaporozhets; Andrey Tolmachev

doi:10.1021/acscombsci.5b00091

2,2,2-Trifluoroethyl Chlorooxoacetate--Universal Reagent for One-Pot Parallel Synthesis of N(1)-Aryl-N(2)-alkyl-Substituted Oxamides

ACS Comb Sci. 2015 Oct 12;17(10):615-22. doi: 10.1021/acscombsci.5b00091. Epub 2015 Sep 14.

Authors

Andrey V Bogolubsky¹, Yurii S Moroz^{1

2}, Pavel K Mykhailiuk^{1

3}, Sergey E Pipko², Anton V Zhemera¹, Anzhelika I Konovets^{1

4}, Olena O Stepaniuk^{1

5}, Inna S Myronchuk^{1

5}, Yurii V Dmytriv¹, Roman A Doroschuk³, Olga A Zaporozhets³, Andrey Tolmachev^{1

2}

Affiliations

¹ Enamine, Ltd. , 78 Chervonotkatska Street, Kyiv, 02094, Ukraine.
² ChemBioCenter, Kyiv National Taras Shevchenko University , 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
³ Department of Chemistry, Kyiv National Taras Shevchenko University , 64 Volodymyrska Street, Kyiv, 01601, Ukraine.
⁴ The Institute of High Technologies, Kyiv National Taras Shevchenko University , 4 Glushkov Street, Building 5, Kyiv, 03187, Ukraine.
⁵ National Technical University of Ukraine "Kyiv Politechnic Institute" , 37 Peremohy Avenue, Kyiv, 03056, Ukraine.

PMID: 26325360
DOI: 10.1021/acscombsci.5b00091

Abstract

A one-pot parallel synthesis of N(1)-aryl-N(2)-alkyl-substituted oxamides with 2,2,2-trifluoroethyl chlorooxoacetate was developed. The synthesis of a library of 45 oxamides revealed higher efficiency of this reagent over the known ethyl chlorooxoacetate. The reagent was successfully used to prepare the known oxamide-containing HIV entry inhibitors.

Keywords: 2,2,2-trifluoroethyl chlorooxoacetate; N1-aryl-N2-alkyl-substituted oxamides; ethyl chlorooxoacetate; one-pot approach; parallel synthesis.

MeSH terms

Amides / chemical synthesis
Amides / chemistry*
Amines / chemical synthesis
Amines / chemistry
Glyoxylates / chemistry*
HIV Fusion Inhibitors / chemical synthesis
Indicators and Reagents
Oxalates / chemistry*
Small Molecule Libraries

Substances

2,2,2-trifluoroethyl chlorooxoacetate
Amides
Amines
Glyoxylates
HIV Fusion Inhibitors
Indicators and Reagents
Oxalates
Small Molecule Libraries