Summary
Racemic N-Boc-4-difluoromethoxyphenylglycine was prepared by O-difluoromethylation of D-N-Boc-4-hydroxyphenylglycine under basic conditions, whereas the hexafluoropropylation reaction gives optically pure D-N-Boc-4-hexafluoropropoxyphenylglycine. D,L-4-difluoromethoxyphenylglycine was obtained by the action of TFA on the corresponding amino acid derivative.
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References
Galushko SV, Grigorjeva MV, Kolycheva MT, Gerus II, Yagupolskii YuL, Kukhar VP (1990) Reversed-phase high performance liquid chromatography of p-polyfluoroalkoxy-(thio)phenylalanine derivatives. Bioorg Khim V 16: 1024–1027
Kolycheva MT, Gerus II, Yagupolskii YuL, Galushko SV, Kukhar VP (1991) Synthesis of optically active p-polyfluoroalkoxy-L-phenylalanines. Z Org Khim V 27: 781–788
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Kolycheva, M.T., Gerus, I.I. & Kukhar, V.P. O-Perfluoroalkylation of 4-hydroxyphenylglycine. Amino Acids 5, 99–101 (1993). https://doi.org/10.1007/BF00806196
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DOI: https://doi.org/10.1007/BF00806196