Robust Synthesis of Trifluoromethionine and Its Derivatives by Reductive Trifluoromethylation of Amino Acid Disulfides by CF3I/Na/Liq.NH3 System.

Abstract We disclose the reductive trifluoromethylation of chemically stable homocystine and cystine to provide corresponding trifluoromethyl ethers by the CF 3 I/Na/Liq.NH 3 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 CF 3 CF 2 I/Na/Liq.NH 3 system.