【结 构 式】 |
【分子编号】55673 【品名】8-Hydroxyoctanoic acid 【CA登记号】 |
【 分 子 式 】C8H16O3 【 分 子 量 】160.21324 【元素组成】C 59.98% H 10.07% O 29.96% |
合成路线1
该中间体在本合成路线中的序号: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.
【1】 Brekle, A.; Hilboll, G.; Lautenschlager, H.-H.; Prop, G.; Welter, A.; Winkelmann, J.; Zierenberg, O. (A. Nattermann & Cie. GmbH); Octanoic acids. DE 3228271; EP 0104342; US 4460598 . |
【2】 Niemann, R.; Lautenschlager, H.H.; Prop, G.; Octimibate Sodium. Drugs Fut 1986, 11, 1, 26. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
55672 | Phenylurea | C7H8N2O | 详情 | 详情 | ||
55673 | 8-Hydroxyoctanoic acid | C8H16O3 | 详情 | 详情 | ||
55674 | Ethyl 8-bromooctanoate; 8-Bromooctanoic acid ethyl ester | C10H19BrO2 | 详情 | 详情 | ||
(I) | 24135 | 2-hydroxy-1,2-diphenyl-1-ethanone; benzoin | 579-44-2 | C14H12O2 | 详情 | 详情 |
(II) | 24136 | 2-chloro-1,4,5-triphenyl-2,3-dihydro-1H-imidazole | C21H17ClN2 | 详情 | 详情 | |
(III) | 24137 | 1,4,5-triphenyl-1,3-dihydro-2H-imidazol-2-one | C21H16N2O | 详情 | 详情 | |
(IV) | 24138 | ethyl 8-[(1,4,5-triphenyl-1H-imidazol-2-yl)oxy]octanoate | C31H34N2O3 | 详情 | 详情 | |
(V) | 24139 | 8-[(1,4,5-triphenyl-1H-imidazol-2-yl)oxy]octanal | C29H30N2O2 | 详情 | 详情 |