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【结 构 式】 
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【分子编号】59801 【品名】3-pentyn-2-ol 【CA登记号】 |
【 分 子 式 】C5H8O 【 分 子 量 】84.11792 【元素组成】C 71.39% H 9.59% O 19.02% |
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：(II)Coupling of methyl 4-acetamido-5-chlorosalicylate (I) with 3-penty-2-ol (II) under Mitsunobu conditions furnished the propargyl ether (III). Acetamide hydrolysis en (III) using H2SO in methanol gave aminoester (IV), whih was further hydrolyzed with NaOH to the carboxylic acid (V). Condensation of racemic acid (V) with the aminopropane (VI) in the presence of DCC afforded the corresponding amide, which was resolved into the enantiomers by means of preparative, chiral HPLC.
| 【1】 Miyazawa, S.; Hibi, S.; Yoshimura, H.; Mori, T.; Hoshino, Y.; Nagai, M.; Kikuchi, K.; Shibata, H.; Hirota, K.; Yamanaka, T.; Yamatsu, I.; Mizuno, M. (Eisai Co., Ltd.); Aminobenzoic acid derivs.. EP 0554794; JP 1994128254; JP 1998007674; US 5389643; US 5578603 . |
| 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) | 59800 | methyl 4-(acetylamino)-5-chloro-2-hydroxybenzoate | C10H10ClNO4 | 详情 | 详情 | |
| (II) | 59801 | 3-pentyn-2-ol | C5H8O | 详情 | 详情 | |
| (III) | 59802 | methyl 4-(acetylamino)-5-chloro-2-[(1-methyl-2-butynyl)oxy]benzoate | C15H16ClNO4 | 详情 | 详情 | |
| (IV) | 59803 | methyl 4-amino-5-chloro-2-[(1-methyl-2-butynyl)oxy]benzoate | C13H14ClNO3 | 详情 | 详情 | |
| (V) | 59804 | 4-amino-5-chloro-2-[(1-methyl-2-butynyl)oxy]benzoic acid | C12H12ClNO3 | 详情 | 详情 | |
| (VI) | 12412 | (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine; (1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-3-ylamine | C8H16N2 | 详情 | 详情 |
Extended Information