Author/Authors :
Patil، نويسنده , , Renukadevi and Li، نويسنده , , Wei and Ross II، نويسنده , , Charles R. and Kraka، نويسنده , , Elfi and Cremer، نويسنده , , Dieter and Mohler، نويسنده , , Michael L. and Dalton، نويسنده , , James T. and Miller، نويسنده , , Duane D.، نويسنده ,
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.
Keywords :
1 , 4-N?O migration , Tetra-n-butylammonium fluoride mediated rearrangement , CsF mediated rearrangement
