Synthesis of 3-isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
https://doi.org/10.29235/1561-8331-2019-55-1-64-68
Abstract
3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione, [cyclo(prolyl-leucyl)], which has a wide range of biological effects, was obtained by thermolysis both the L-prolyl-L-leucine methyl ester and the methyl ester L-leucyl-L-proline, for the synthesis of which the removal of tert-butyloxycarbonyl amino protecting groups in tert-butyloxycarbonylprolyl-leucine methyl ester and tert-butyloxycarbonylleucyl-proline methyl ester under the action of a methanolic solution of hydrogen chloride and the treatment of the resulting of methyl esters hydrochlorides L-prolyl-L-leucine and L-leucyl-L-proline with an equimolar amount of triethylamine were used. The starting tert-butyloxycarbonylleucyl-proline methyl ester was prepared like the previously synthesized tert-butyloxycarbonylprolyl-leucine methyl ester by the carbodiimide method. It was found that the cyclization of the methyl ester of L-leucyl-L-proline into the desired diketopiperazine proceeds at a lower temperature than the cyclization of the methyl ester of L-prolyl-L-leucine.
About the Authors
V. A. Haidukevich
Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
VeranikaA. Haidukevich – JuniorResearch, Postgraduatestudent.
13, Surganov Str., 220072, Minsk.
I. V. Rudziankova
Institute of Physiology of the National Academy of Sciences of Belarus
Belarus
Belarus
Iryna V. Rudziankova – Junior Research, Postgraduate student.
28, Academic Str., 220072, Minsk.
L. A. Popova
Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Ludmila A. Popova – Senior Research.
13, Surganov Str., 220072, Minsk.
Z. P. Zubreichuk
Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Zinaida P. Zubreichuk – Senior Research.
13, Surganov Str., 220072, Minsk.
L. N. Nikalayevich
Institute of Physiology of the National Academy of Sciences of Belarus
Belarus
Belarus
Larysa N. Nikalayevich – Ph. D. (Biological), Assistant Professor, Head of the Laboratory of Cell Technology.
28, Academic Str., 220072, Minsk.
V. A. Knizhnikov
Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Valeriy A. Knizhnikov – D. Sc. (Chemistry), Head of the Laboratory of Amino Acid Derivatives.
13, Surganov Str., 220072, Minsk.
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