Registration Number
0225U000745,
(0124U000139)
, R & D reports
Title
Development of a method for the synthesis of heterocycles with chiral substituents from the corresponding alpha-amino acids
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Розробка лабораторної методики синтезу діазокетонів N-Boc захищених α-амінокислот та її масштабування.
Head
Kompanets Mikhaylo O., Кандидат хімічних наук
Registration Date
18-01-2025
Organization
Institute of Physical and Organic Chemistry and Coal Chemistry. LM Litvinenko of the National Academy of Sciences of Ukraine
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Development of a method for the synthesis of a series of heterocycles with chiral substituents by creating a diazoketone from commercially available Boc-protected amino acids. The synthesis technique will be easily scalable within 1-10 g without significant equipment changes with the possibility of certain stages automation.
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The object of the study is diazoketones formed from natural corresponding amino acids with a protected amino group. The aim of the work is to verify, optimize and develop methods for obtaining diazoketones from natural corresponding amino acids using various protection on the amino group. For this purpose, the following methods were used - methods of organic synthesis, mass and NMR spectroscopy. As part of the study, the synthesis and optimization of purification methods of a number of protected amino acids with a protected amino group were carried out. The following protective groups were used: tert-butyloxycarbonyl, benzyloxycarbonyl, fluorenylmethyloxycarbonyl and phthalimide groups. The synthesis of diazoketones from amino acids with various protection of the amino group was carried out under the conditions of using various activating agents of the carboxyl group. A method for activating the carboxyl group using N-propylphosphonium anhydride in the addition reaction to diazomethane was developed. The activator almost completely suppresses the formation of side methyl esters and is easily removed from the reaction mixture by treatment with water.
Product Description
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Akopov Oleksii V.
Anishсhenko Viktor M.
Anishсhenko Hanna V.
Volkova Larysa K.
Dykun Oleksii M.
Kompanets Olena O.
Redko Andrii M.
Khyzhan Oleksandr I.
Shendrik Tetiana H.
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2025-01-18
