Octimibate
辛米贝特Chemical Name: 8-[(1,4,5-Triphenyl-1H-imidazol-2yl)oxy]octanoic acid
CAS No. 89838-96-0, 89839-10-1 (Na salt)
项目整合开发状态: Phase I
项目研究机构: Nattermann (Originator)
合成路线:Condensation of benzoin (I) and phenylurea in a boiling mixture of glacial acetic acid and 63% hydrobromic acid yields 1,4,5-triphenyl-4-imidazolin-2-one (III),which can be converted to octimibate (VI) and octimibate sodium by two procedures (A,B):Procedure A: (III) is converted to 2-chloro-1,4,5-triphenylimidazole (II) on treatment with phosphorus oxytrichloride at 100 C.Octimibate is prepared by treatment of (II) with the dipotassium salt of 8-hydroxyoctanoic acid in boiling dimethylformamide.Procedure B: The sodium salt of (III) is formed by treatment with sodium hydride in dimetbylformamide.The reaction of this salt with 8-bromooctanoic acid ethyl ester gives 8-[(1,4,5-triphenylimidazol-2yl)oxy]octanoic acid ethyl ester (IV) after purification using column chromatography.Saponification of (IV) yields octimibate (V),which is converted to octimibate sodium.
📌 参考资料/链接：
参考文献标题:Octanoic acids
文献作者:Brekle,A.; Hilboll,G.; Lautenschl鋑er,H.-H.; Prop,G.; Welter,A.; Winkelmann,J.; Zierenberg,O.(A.Nattermann & Cie.GmbH)
参考来源:DE 3228271; EP 0104342; US 4460598
📄 详细内容
合成路线:Condensation of benzoin (I) and phenylurea in a boiling mixture of glacial acetic acid and 63% hydrobromic acid yields 1,4,5-triphenyl-4-imidazolin-2-one (III),which can be converted to octimibate (VI) and octimibate sodium by two procedures (A,B):Procedure A: (III) is converted to 2-chloro-1,4,5-triphenylimidazole (II) on treatment with phosphorus oxytrichloride at 100 C.Octimibate is prepared by treatment of (II) with the dipotassium salt of 8-hydroxyoctanoic acid in boiling dimethylformamide.Procedure B: The sodium salt of (III) is formed by treatment with sodium hydride in dimetbylformamide.The reaction of this salt with 8-bromooctanoic acid ethyl ester gives 8-[(1,4,5-triphenylimidazol-2yl)oxy]octanoic acid ethyl ester (IV) after purification using column chromatography.Saponification of (IV) yields octimibate (V),which is converted to octimibate sodium.
参考文献标题:Octimibate Sodium
文献作者:Niemann,R.; Lautenschl鋑er,H.H.; Prop,G.
参考来源:Drugs Fut 1986,11(1),26
产品链接: CAS No. 89838-96-0››