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【结 构 式】 
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【分子编号】52312 【品名】2-(4-Isobutylphenyl)propionic acid; Ibuprofen 【CA登记号】15687-27-1 |
【 分 子 式 】C13H18O2 【 分 子 量 】206.28472 【元素组成】C 75.69% H 8.8% O 15.51% |
合成路线1
该中间体在本合成路线中的序号：(I)Formation in anhydrous medium of the acyl halide (II) of dl-2-(4'-isobutylphenyl)propionic acid (I) with phosphorous or sulfur halides or oxyhalides, and the subsequent reaction in anhydrous medium with beta-hydroxyethylamine (III) to give N-(beta-hydroxyethyl)-dl-2-(4’-isobutylphenyl)propionamide.
| 【1】 McKenney, D.; et al.; Aminoprofen. Drugs Fut 1981, 6, 10, 599. |
合成路线2
该中间体在本合成路线中的序号：(I)By esterification of 2-(p-isobutylphenyl)propionic acid (I) with ethanol and H2SO4 at reflux temperature yielding the corresponding ethyl ester (II), which is the treated with hydroxylamine in refluxing methanol
| 【1】 Orzalesi, G.; Selleri, R. (Manetti&Roberts); DE 2400531; FR 2213062 . |
| 【2】 Castaner, J.; Arrigoni, Martelli, E.; Ibuproxam. Drugs Fut 1977, 2, 12, 808. |
合成路线3
该中间体在本合成路线中的序号：(I)Coupling of ibuprofen (I) with N-acetylcysteine (II) via activation with carbonyl diimidazole produced the thioester adduct (III). Reaction of the free carboxyl group of (III) with tetrahydrofuran in the presence of triphenylphosphine and carbon tetrabromide gave rise to the bromobutyl ester (IV). The bromide group of (IV) was finally displaced with silver nitrate to produce the title nitrate ester.
| 【1】 Del Soldato, P. (NicOx SA); Pharmaceutical cpds.. EP 1169294; WO 0061537 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 52312 | 2-(4-Isobutylphenyl)propionic acid; Ibuprofen | 15687-27-1 | C13H18O2 | 详情 | 详情 |
| (II) | 39365 | (2S)-2-(acetamido)-3-sulfanylpropionic acid | 616-91-1 | C5H9NO3S | 详情 | 详情 |
| (III) | 52313 | N-acetyl{2-[4-(2-methylpropyl)phenyl]propanoyl}cysteine | C18H25NO4S | 详情 | 详情 | |
| (IV) | 52314 | 4-bromobutyl 2-(acetylamino)-3-({2-[4-(2-methylpropyl)phenyl]propanoyl}sulfanyl)propanoate | C22H32BrNO4S | 详情 | 详情 |