Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid
| Autor: | Vadim A. Soloshonok, Hiroyuki Konno, Ryosuke Takeda, Takahiro Hiramatsu, Hiroki Moriwaki, Xinyi Liu, Jianlin Han, Hidenori Abe |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Alkylation
Hydrocarbons Fluorinated asymmetric synthesis large-scale synthesis Pharmaceutical Science Article Ni complex Analytical Chemistry chemistry.chemical_compound Drug Discovery Moiety Physical and Theoretical Chemistry Chiral auxiliary Schiff base Molecular Structure glycine Schiff base Organic Chemistry Enantioselective synthesis Stereoisomerism fluorinated amino acid Combinatorial chemistry Butyrates chemistry Chemistry (miscellaneous) Glycine Molecular Medicine Bioisostere Leucine |
| Zdroj: | Molecules Volume 24 Issue 24 |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules24244521 |
| Popis: | Enantiomerically pure derivatives of 2-amino-4,4,4-trifluorobutanoic acid are in great demand as bioisostere of leucine moiety in the drug design. Here, we disclose a method specifically developed for large-scale (> 150 g) preparation of the target (S)-N-Fmoc-2-amino-4,4,4-trifluorobutanoic acid. The method employs a recyclable chiral auxiliary to form the corresponding Ni(II) complex with glycine Schiff base, which is alkylated with CF3&ndash CH2&ndash I under basic conditions. The resultant alkylated Ni(II) complex is disassembled to reclaim the chiral auxiliary and 2-amino-4,4,4-trifluorobutanoic acid, which is in situ converted to the N-Fmoc derivative. The whole procedure was reproduced several times for consecutive preparation of over 300 g of the target (S)-N-Fmoc-2-amino-4,4,4-trifluorobutanoic acid. |
| Databáze: | OpenAIRE |
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