ChemicalBook CAS DataBase List Bicalutamide

Bicalutamide synthesis

11synthesis methods

Product Name:Bicalutamide
CAS Number:90357-06-5
Molecular formula:C18H14F4N2O4S
Molecular Weight:430.38

90356-78-8 Synthesis

N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide

90356-78-8
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90357-06-5
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Yield:90357-06-5 100%

Reaction Conditions:

Stage #1: N-(4-Cyano-3-trifluoromethyl-phenyl)-3-(4-fluoro-phenylsulfanyl)-2-hydroxy-2-methyl-propionamidewith potassium permanganate;tetrabutylammonium hydrogensulfate in water monomer;ethyl acetate at 25 - 30; for 2.5 h;
Stage #2: with disodium metabisulfite in water monomer;ethyl acetate; for 1 h;

Steps:

1

A triphasic mixture of compound of formula 4 (250.Og, 0.627mol), potassium permanganate (253.Og, 1.56mol), ethyl acetate (1500ml), water (2500ml) and tetrabutyl ammonium hydrogen sulfate (21.28g, 0.0627mol) was stirred for 2.5 hours at 25-3O⁰C. A solution of sodium metabisulfite (75Og) in water (1500ml) was then added, followed by ethyl acetate ( 1000ml). The mixture stirred for lhour, the insoluble inorganic material is filtered, and the upper organic layer containing product was separated. The organic layer was washed sequentially with 5% HCl solution and water, concentrated and degassed under vacuum to obtain bicalutamide, 27Og (100% yield).Purification: A suspension of bicalutamide (376g) in 2-propanol (3.761it) was heated to reflux for 2 hours, and then gradually cooled to ambient temperature. The resultant slurry was filtered, washed with 2-propanol and dried at about 50⁰C to obtain bicalutamide of HPLC purity 99.79%.

References:

WO2007/13094,2007,A2 Location in patent:Page/Page column 10