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Bicalutamide, ICI-176334, Raffolutil, Casodex

比卡鲁胺Chemical Name: (?-4-[3-(4-Fluorophenylsulfonyl)-2-hydroxy-2-methylpropionamido]-2-(trifluoromethyl)benzonitrile
CAS No. 90357-06-5
项目整合开发状态: Launched-1995
项目研究机构: AstraZeneca (Originator)
合成路线:Coupling of methacryloyl chloride (I) with substituted aniline (II) in dimethylacetamide yields amide (III),which is then converted into the epoxy derivative (IV) by oxidation with m-chloroperbenzoic acid (mCPBA) and 4-methyl-2,6-di-tert-butylphenol (A) in refluxing 1,1,1-trichloroethane.Condensation of (IV) with thiol (V) by means of NaH in THF provides fluorophenylthio derivative (VI),which is finally oxidized with mCPBA in CH2Cl2 to furnish the desired compound trichloroethane.
📌 参考资料/链接:
参考文献标题:Amide derivs.
文献作者:Tucker,H.(AstraZeneca plc)
参考来源:EP 0100172; JP 1990131462; US 4636505

📄 详细内容


合成路线:Coupling of methacryloyl chloride (I) with substituted aniline (II) in dimethylacetamide yields amide (III),which is then converted into the epoxy derivative (IV) by oxidation with m-chloroperbenzoic acid (mCPBA) and 4-methyl-2,6-di-tert-butylphenol (A) in refluxing 1,1,1-trichloroethane.Condensation of (IV) with thiol (V) by means of NaH in THF provides fluorophenylthio derivative (VI),which is finally oxidized with mCPBA in CH2Cl2 to furnish the desired compound trichloroethane.

参考文献标题:Nonsteroidal antiandrogens.Synthesis and structure-activity relationships of 3-substituted derivatives of 2-hydroxypropionanilides
文献作者:Tucker,H.; Crook,J.W.; Chesterson,G.J.
参考来源:J Med Chem 1988,31(5),954


合成路线:The reaction of 4-amino-2-(trifluoromethyl)benzonitrile (I) with 2-oxopropionic acid (II) by means of SOCl2 gives the corresponding amide (III),which is finally condensed with the methyl sulfone (IV) by means of BuLi in THF.
参考文献标题:A two-step synthesis of the anti-cancer drug (R,S)-bicalutamide
文献作者:Ekwuribe,N.N.; James,K.D.
参考来源:Synthesis (Stuttgart) 2002,(7),850


产品链接: CAS No. 90357-06-5››