Cesium fluoride and tetra-n-butylammonium fluoride mediated 1,4-N-->O shift of disubstituted phenyl ring of a bicalutamide derivative.
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.
Patil
Renukadevi
R
Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, 847 Monroe Avenue, Room 327, Memphis, TN 38163, USA.
Li
Wei
W
Ross
Charles R
CR
Kraka
Elfi
E
Cremer
Dieter
D
Mohler
Michael L
ML
Dalton
James T
JT
Miller
Duane D
DD