Efficient synthesis of 5-(hydroxymethyl)piperazin-2-ones using automatically prepared chiral bromocarboxylic acid and Garner’s aldehyde as versatile building blocks
| Autor: | Takashi Takahashi, Hisashi Masui, Akira Kusayanagi, Mai Minoshima, Sae Yosugi, Mitsuru Shoji, Kohei Naito |
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| Rok vydání: | 2021 |
| Předmět: |
Clinical Biochemistry
Pharmaceutical Science 01 natural sciences Biochemistry Aldehyde Piperazines chemistry.chemical_compound Drug Discovery Hydroxymethyl Amino Acids Molecular Biology chemistry.chemical_classification Aldehydes Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry Stereoisomerism Combinatorial chemistry 0104 chemical sciences 010404 medicinal & biomolecular chemistry Cyclization Reagent Molecular Medicine Oxidation-Reduction Automated method |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 40:127961 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2021.127961 |
| Popis: | An efficient method for the synthesis of substituted 5-(hydroxymethyl)piperazin-2-ones was established by using an automated synthesis process. Thirteen piperazinones were synthesized from chiral α-bromocarboxylic acids and Garner's aldehyde which were prepared by using our originally developed automated synthesizer, ChemKonzert®. The automated method of synthesizing chiral α-bromocarboxylic acids was efficient and safe because the rate of the dropwise addition of the reagent can be controlled using the automated synthesizer. This method is expected to contribute to the synthesis of pharmaceuticals. |
| Databáze: | OpenAIRE |
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