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【结 构 式】

【分子编号】16704

【品名】phenethyl acetate; Phenylethyl-(2) Acetate

【CA登记号】103-45-7

【 分 子 式 】C10H12O2

【 分 子 量 】164.20408

【元素组成】C 73.15% H 7.37% O 19.49%

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:(I)

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
Extended Information