Robust synthesis of trifluoromethionine and its derivatives by reductive trifluoromethylation of amino acid disulfides by CF3I/Na/Liq.NH3 system
Robust synthesis of trifluoromethionine and its derivatives by reductive trifluoromethylation of amino acid disulfides by CF3I/Na/Liq.NH3 system
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DOI：
10.1016/j.jfluchem.2011.01.001
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发表时间：
2011-03
影响因子：
1.9
通讯作者：
H. Yasui;Takeshi Yamamoto;Etsuko Tokunaga;N. Shibata
中科院分区：
文献类型：
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作者：
H. Yasui;Takeshi Yamamoto;Etsuko Tokunaga;N. Shibata
我们公开了通过CF 3 I/Na/Liq·NH 3体系还原化学稳定的高胱氨酸和胱氨酸的三氟甲基化以提供相应的三氟甲基醚。在相同的条件下，未保护的和保护的高胱氨酸都可以很好地转化为三氟甲基化甲硫氨酸。所描述的方法提供了一种适用于多克合成的药学上重要的三氟甲基噻吩的稳健合成。高胱氨酸的五氟乙基化反应也可通过CF_3CF_2I/Na/Liq.NH_3体系实现。
We disclose the reductive trifluoromethylation of chemically stable homocystine and cystine to provide corresponding trifluoromethyl ethers by the CF3I/Na/Liq.NH3system. 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.NH3system.