title: Cesium fluoride and tetra-n-butylammonium fluoride mediated 1,4-N-->O shift of disubstituted phenyl ring of a bicalutamide derivative.
abstract: A novel 1,4-N-->O migration of a disubstituted phenyl ring was observed during N-methylation of a bicalutamide derivative, (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide, in the presence of CsF-Celite/acetonitrile and desilylation of (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2,N-dimethylpropionamide in tetra-n-butylammonium fluoride/THF. Both NMR and X-ray analysis confirmed the structure of the 1,4-N-->O disubstituted phenyl ring migrated product.
authors: Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, 847 Monroe Avenue, Room 327, Memphis, TN 38163, USA.
authors: Renukadevi
authors: R
authors: Patil
authors: Wei
authors: W
authors: Li
authors: Charles R
authors: CR
authors: Ross
authors: Elfi
authors: E
authors: Kraka
authors: Dieter
authors: D
authors: Cremer
authors: Michael L
authors: ML
authors: Mohler
authors: James T
authors: JT
authors: Dalton
authors: Duane D
authors: DD
authors: Miller