Studies on organophosphorus compounds 101. A facile synthetic route to trifluoromethylated aminophosphonic acids and phosphonopeptides

✍ Scribed by Chengye Yuan; Yixin Zhang; Wenchen Luo; Zipeng Yao

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 181 KB
• Volume: 9
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1998)9:2<139::aid-hc7>3.0.co;2-7

✦ Synopsis

A series of dialkyl 1-(N-substituted amino)-2,2,2-trifluoroethylphosphonates was synthesized by Arbuzovtype reactions involving an N-substituted trifluoromethylimidoyl chloride and the appropriate trialkyl phosphite. The resulting C‫ס‬N bond was successfully hydrogenated by NaBH 4 CN treatment. The subsequent deprotection of the amino group was conducted either by hydrogenolysis with Pd black or by use of cerium ammonium nitrate, depending on the structure of the substituent on the amino function. The free amino group thus obtained underwent a coupling reaction with an aminoacyl chloride in the usual manner.