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【结 构 式】 
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【分子编号】16713 【品名】2-amino-2-(4-octylphenethyl)-1,3-propanediol 【CA登记号】162359-55-9 |
【 分 子 式 】C19H33NO2 【 分 子 量 】307.47656 【元素组成】C 74.22% H 10.82% N 4.56% O 10.41% |
合成路线1
该中间体在本合成路线中的序号：(X)The Friedel-Crafts condensation of phenethyl acetate (I) with octanoyl chloride (II) by means of AlCl3 in dichloroethane gives 2-(4-octanoylphenyl)ethyl acetate (III), which is reduced with triethylsilane in TFA to afford 2-(4-octylphenyl)ethyl acetate (IV). The deprotection of (IV) with sodium ethoxide in ethanol gives 2-(4-octylphenyl)ethanol (V), which is treated with methanesulfonyl chloride followed by sodium iodide in refluxing 2-butanone yielding 2-(4-octylphenyl)ethyl iodide (VI). The condensation of (VI) with diethylacetamidomalonate (VII) by means of sodium ethoxide in ethanol/THF gives diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate (VIII), which is reduced with LiAlH4 in THF and treated with acetic anhydride in pyridine to afford 2-acetamido-2-(acetoxymethyl)-4-(4-octylphenyl)butyl acetate (IX). The hydrolysis of (IX) with lithium hydroxide in refluxing methanol/water gives 2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol (X), which is finally treated with HCl in diethyl ether.
| 【1】 Chiba, K.; Adachi, K.; FTY720. Drugs Fut 1997, 22, 1, 18. |
| 【2】 Fujita, T.; Sasaki, S.; Yoneta, M.; Mishina, T.; Adachi, K.; Chiba, K. (Taito Co., Ltd.; Welfide Corporation); 2-Amino-1,3-propanediol compound and immunosuppressant. EP 0627406; JP 1994509845; US 5719176; WO 9408943 . |
| 【3】 Kiuchi, M.; Adachi, K.; Kohara, T.; et al.; Synthesis and immunosuppressive activity of 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols. J Med Chem 2000, 43, 15, 2946. |
| 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) | 16704 | phenethyl acetate; Phenylethyl-(2) Acetate | 103-45-7 | C10H12O2 | 详情 | 详情 |
| (II) | 11123 | Octanoyl chloride; n-Caprylyl chloride;Capryloyl chloride | 111-64-8 | C8H15ClO | 详情 | 详情 |
| (III) | 16706 | 4-octanoylphenethyl acetate | C18H26O3 | 详情 | 详情 | |
| (IV) | 16707 | 4-octylphenethyl acetate | C18H28O2 | 详情 | 详情 | |
| (V) | 16708 | 2-(4-octylphenyl)-1-ethanol | C16H26O | 详情 | 详情 | |
| (VI) | 16709 | 1-[4-(2-iodoethyl)phenyl]octane | C16H25I | 详情 | 详情 | |
| (VII) | 16710 | Diethyl 2-(acetamido)malonate; Diethyl acetamidomalonate | 1068-90-2 | C9H15NO5 | 详情 | 详情 |
| (VIII) | 16711 | diethyl 2-(acetamido)-2-(4-octylphenethyl)malonate | C25H39NO5 | 详情 | 详情 | |
| (IX) | 16712 | 2-(acetamido)-2-[(acetoxy)methyl]-4-(4-octylphenyl)butyl acetate | C25H39NO5 | 详情 | 详情 | |
| (X) | 16713 | 2-amino-2-(4-octylphenethyl)-1,3-propanediol | 162359-55-9 | C19H33NO2 | 详情 | 详情 |