STUDIES ON ORGANOPHOSPHORUS COMPOUNDS 101 - A FACILE SYNTHETIC ROUTE TO TRIFLUOROMETHYLATED AMINOPHOSPHONIC ACIDS AND PHOSPHONOPEPTIDES

A series of dialkyl 1-(N-substituted amino)-2,2,2-trifluoroethylphosph onates was synthesized by Arbuzov-type reactions involving an N-substi tuted trifluoromethylimidoyl chloride and the appropriate trialkyl pho sphite. The resulting C=N bond was successfully hydrogenated by NaBH4C N treatment. The subsequent deprotection of the amino group was conduc ted either by hydrogenolysis with Pd black or by use of cerium ammoniu m nitrate, depending on the structure of the substituent on the amino function. The free amino group thus obtained underwent a coupling reac tion with an aminoacyl chloride in the usual manner. (C) 1998 John Wil ey & Sons, Inc.