Cesium fluoride and tetra-n-butylammonium fluoride mediated 1,4-N→O shift of disubstituted phenyl ring of a bicalutamide derivative

Renukadevi Patil, Wei Li, Charles R. Ross, Elfi Kraka, Dieter Cremer, Michael L. Mohler, James T. Dalton, Duane Miller

Research output: Contribution to journalArticle

14 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)3941-3944
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number23
DOIs
StatePublished - Jun 5 2006

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Diatomaceous Earth
Methylation
X ray analysis
Fluorides
Nuclear magnetic resonance
X-Rays
Derivatives
acetonitrile
bicalutamide
cesium fluoride

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Cesium fluoride and tetra-n-butylammonium fluoride mediated 1,4-N→O shift of disubstituted phenyl ring of a bicalutamide derivative. / Patil, Renukadevi; Li, Wei; Ross, Charles R.; Kraka, Elfi; Cremer, Dieter; Mohler, Michael L.; Dalton, James T.; Miller, Duane.

In: Tetrahedron Letters, Vol. 47, No. 23, 05.06.2006, p. 3941-3944.

Research output: Contribution to journalArticle

Patil, Renukadevi ; Li, Wei ; Ross, Charles R. ; Kraka, Elfi ; Cremer, Dieter ; Mohler, Michael L. ; Dalton, James T. ; Miller, Duane. / Cesium fluoride and tetra-n-butylammonium fluoride mediated 1,4-N→O shift of disubstituted phenyl ring of a bicalutamide derivative. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 23. pp. 3941-3944.
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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.",
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T1 - Cesium fluoride and tetra-n-butylammonium fluoride mediated 1,4-N→O shift of disubstituted phenyl ring of a bicalutamide derivative

AU - Patil, Renukadevi

AU - Li, Wei

AU - Ross, Charles R.

AU - Kraka, Elfi

AU - Cremer, Dieter

AU - Mohler, Michael L.

AU - Dalton, James T.

AU - Miller, Duane

PY - 2006/6/5

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N2 - 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.

AB - 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.

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