Open Access
Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid
Тип публикации: Journal Article
Дата публикации: 2019-12-10
PubMed ID:
31835583
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Краткое описание
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.
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ГОСТ
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Han J. et al. Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid // Molecules. 2019. Vol. 24. No. 24. p. 4521.
ГОСТ со всеми авторами (до 50)
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Han J., Takeda R., Liu X., Konno H., Abe H., Hiramatsu T., Moriwaki H., Soloshonok V. A. Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid // Molecules. 2019. Vol. 24. No. 24. p. 4521.
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RIS
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TY - JOUR
DO - 10.3390/molecules24244521
UR - https://doi.org/10.3390/molecules24244521
TI - Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid
T2 - Molecules
AU - Han, Jianlin
AU - Takeda, Ryosuke
AU - Liu, Xinyi
AU - Konno, Hiroyuki
AU - Abe, Hidenori
AU - Hiramatsu, Takahiro
AU - Moriwaki, Hiroki
AU - Soloshonok, Vadim A.
PY - 2019
DA - 2019/12/10
PB - MDPI
SP - 4521
IS - 24
VL - 24
PMID - 31835583
SN - 1420-3049
ER -
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@article{2019_Han,
author = {Jianlin Han and Ryosuke Takeda and Xinyi Liu and Hiroyuki Konno and Hidenori Abe and Takahiro Hiramatsu and Hiroki Moriwaki and Vadim A. Soloshonok},
title = {Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid},
journal = {Molecules},
year = {2019},
volume = {24},
publisher = {MDPI},
month = {dec},
url = {https://doi.org/10.3390/molecules24244521},
number = {24},
pages = {4521},
doi = {10.3390/molecules24244521}
}
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MLA
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Han, Jianlin, et al. “Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid.” Molecules, vol. 24, no. 24, Dec. 2019, p. 4521. https://doi.org/10.3390/molecules24244521.