Uliprisnil acetate, RTI-3021-012, CDB-2914

醋酸乌利司他Chemical Name: 17alpha-Acetoxy-11beta-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione
CAS No. 126784-99-4
项目整合开发状态: Phase I
项目研究机构: Research Triangle Institute (Originator), Population Council (Not Determined)
合成路线:The reaction of cyanohydrineketal (I) with dimethyl(chloromethyl)silyl chloride (A),TEA and DMAP in THF gives the silylated cyanohydrine (II),which is treated with Li and 4,4'-di-tert-butylbiphenyl (DBB) in THF followed by acidification with HCl yields 17alpha-hydroxy-19-norpregna-4,9-diene-3,20-dione (III).The reaction of (III) with ethylene-glycol and TsOH afford the bis ethylenedioxy derivative (IV),which is epoxidized with H2O2 and trifluoroacetone in dichloromethane affording the monoepoxide (V).The Grignard condensation of (V) with 4-(dimethylamino)phenylmagnesium bromide in THF provides the 11-beta-(dimethylamino) derivative (VII),which is dehydrated and deprotected with sulfuric acid in refluxing ethanol to furnish 11-beta-[4-(dimethylamino)phenyl]-17alpha-hydroxy-19-norpregna-4,9-diene-3,20-dione (VIII).Finally,this compound is acetylated with AcOH and trifluoroacetic anhydride in dichloromethane.