【结 构 式】 |
【分子编号】43263 【品名】2-[(10-undecenylamino)carbonyl]phenyl acetate 【CA登记号】 |
【 分 子 式 】C20H29NO3 【 分 子 量 】331.4552 【元素组成】C 72.47% H 8.82% N 4.23% O 14.48% |
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:(VI)Conversion of 10-undecen-1-ol (I) into the primary amine (IV) was effected by Mitsunobu coupling of (I) with phthalimide (II), followed by hydrazinolysis of the resulting N-(10-undecenyl)phthalimide (III). Amine (IV) was then acylated with O-acetylsalicyloyl chloride (V) to give salicylamide (VI). Oxidative cleavage of the terminal olefin to the carboxylic acid (VII) was achieved using potassium permanganate under phase-transfer conditions. The O-acetyl group was finally removed by treatment with NaOH.
【1】 Leone-Bay, A.; Paton, D.R.; Freeman, J.; et al.; Synthesis and evaluation of compounds that facilitate the gastrointestinal absorption of heparin. J Med Chem 1998, 41, 7, 1163. |
【2】 Leone-Bay, A.; Ho, K.-K.; Sarubbi, D.J.; Milstein, S.J.; Press, J.B. (Emisphere Technologies, Inc.); Cpds. and compsns. for delivering active agents. US 5650386; WO 9630036 . |
【3】 Leone-Bay, A. (Emisphere Technologies, Inc.); Cpds. and compsns. for delivering active agents. WO 9736480 . |
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) | 43260 | 10-undecen-1-ol | 112-43-6 | C11H22O | 详情 | 详情 |
(II) | 12376 | Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione | 85-41-6 | C8H5NO2 | 详情 | 详情 |
(III) | 43261 | 2-(10-undecenyl)-1H-isoindole-1,3(2H)-dione | C19H25NO2 | 详情 | 详情 | |
(IV) | 43262 | 10-undecenylamine; 10-undecen-1-amine | C11H23N | 详情 | 详情 | |
(V) | 16900 | 2-(chlorocarbonyl)phenyl acetate; Acetylsalicyloyl chloride | 5538-51-2 | C9H7ClO3 | 详情 | 详情 |
(VI) | 43263 | 2-[(10-undecenylamino)carbonyl]phenyl acetate | C20H29NO3 | 详情 | 详情 | |
(VII) | 43264 | 10-[[2-(acetoxy)benzoyl]amino]decanoic acid | C19H27NO5 | 详情 | 详情 |
Extended Information