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【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%

与该中间体有关的原料药合成路线共 1 条

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
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