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- Title
Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid.
- Authors
Han, Jianlin; Takeda, Ryosuke; Liu, Xinyi; Konno, Hiroyuki; Abe, Hidenori; Hiramatsu, Takahiro; Moriwaki, Hiroki; Soloshonok, Vadim A.; Chinchilla, Rafael; Dembinski, Roman
- Abstract
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–CH2–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.
- Subjects
ENANTIOMERIC purity; SCHIFF bases; DRUG design; GLYCINE; ACIDS; ACID derivatives; ASYMMETRIC synthesis
- Publication
Molecules, 2019, Vol 24, Issue 24, p4521
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules24244521