Robust synthesis of trifluoromethionine and its derivatives by reductive trifluoromethylation of amino acid disulfides by CF3I/Na/Liq.NH3 system |
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| Authors: | Hiroyuki Yasui |
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| Institution: | Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan |
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| Abstract: | We disclose the reductive trifluoromethylation of chemically stable homocystine and cystine to provide corresponding trifluoromethyl ethers by the CF3I/Na/Liq.NH3 system. Both non-protected and protected homocystines can be nicely converted into trifluoromethylated methionines under the same condition. The method described offers a robust synthesis of pharmaceutically important trifluoromethionine, suitable for multigram synthesis. Pentafluoroethylation of homocystine was also achieved by the CF3CF2I/Na/Liq.NH3 system. |
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| Keywords: | Reductive trifluoromethylation Trifluoromethionine Amino acid Disulfide Antiamebic drug Pentafluoroethylation |
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