New reactions of polyfluoroaromatic compounds. Pentafluorophenylalanine and tetrafluorotyrosine

R Filler, NR Ayyangar, W Gustowski…

文献索引：Filler,R. et al. Journal of Organic Chemistry, 1969 , vol. 34, # 3 p. 534 - 538

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被引用次数: 34

摘要

The reaction of a-bromo-p-pentafluorophenylpropionic acid (4) with ammonia gives trans-4- amino-2, 3, 5, 6-tetrafluorocinnamic acid (5), rather than pentafluorophenylalanine (1). Compound 1 is prepared by hydrogenolysis of a-azido-p-pentafluorophenylpropionic acid, by reductive hydrolysis of the azlactone precursor, and by the acetamidomalonate procedure (the method of choice). Tetrafluorotyrosine (2) is prepared in 17% over-all yield ...