One-step construction of peptidomimetic 5-carbamoyl-4-sulfonyl-2- piperazinones

Journal of Combinatorial Chemistry

Volumn 7, Issue 3, 2005, Pages 360-363

  Ilyin, Alexei P ^a   Trifilenkov, Andrey S ^a   Kurashvili, Irina D ^a   Krasavin, Mikhail ^a   Ivachtchenko, Alexandre V ^b  

^a Chemical Diversity Research Institute   (Russian Federation)

^b CHEMDIV INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERAZINE DERIVATIVE;

ARTICLE; COMBINATORIAL CHEMISTRY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PEPTIDES; PIPERAZINES;

EID: 20044388356     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0500147     Document Type: Article

References (24)

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21. The final 5-carbamoyl-4-sulfonyl-2-piperazinones 4 were prepared according to the following general procedure: A solution of an N-sulfonyl-N-(2-oxopropyl)glycine 1 (1 mmol), a primary aromatic or aliphatic amine 2 (1 mmol), and an isonitrile 3 (1 mmol) in anhydrous methanol (3-5 mL) was stirred at room temperature for 8 h. The precipitate formed was separated by filtration; washed with a small amount of cold methanol, followed by ether; and air-dried (in the cases when the product did not precipitate from the reaction mixture, the solvent was removed in vacuo, and the residue was then solidified upon addition of a small amount of ether prior to filtration). The yield of the obtained solid products was 45-75% with at least 95% purity, as demonstrated by LC/MS analysis.
22. The keto acids 1 used in this study are commercially available from ChemDiv. Inc. (http://www.chemdiv.com).
23. 1H NMR spectroscopy.
24. Our preliminary results on similar multicomponent reactions involving ketocarboxylic acids derived from α-amino acids other than glycine indicated that such processes provide the desired products as mixtures of diastereomers. Because the latter were found difficult to separate, a possibility of attaining some degree of diastereocontol is being currently investigated.