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Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid.


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.

SUBMITTER: Han J 

PROVIDER: S-EPMC6943542 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Preparative Method for Asymmetric Synthesis of (<i>S</i>)-2-Amino-4,4,4-trifluorobutanoic Acid.

Han Jianlin J   Takeda Ryosuke R   Liu Xinyi X   Konno Hiroyuki H   Abe Hidenori H   Hiramatsu Takahiro T   Moriwaki Hiroki H   Soloshonok Vadim A VA  

Molecules (Basel, Switzerland) 20191210 24


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 (<i>S</i>)-<i>N</i>-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 CF<sub>3</sub>-CH<sub>2</sub>-I under basic condi  ...[more]

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