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【结 构 式】

【分子编号】10399

【品名】3-Ethoxy-4-(pentyloxy)benzoic acid

【CA登记号】

【 分 子 式 】C14H20O4

【 分 子 量 】252.3104

【元素组成】C 66.65% H 7.99% O 25.36%

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)

This compound can be obtained by three related ways: 1) The carboxylation of 3-ethoxy-4-pentyloxyiodobenzene (I) with CO2 and butyllithium in ether gives 3-ethoxy-4-pentyloxybenzoic acid (II), which is reduced with LiAlH4 in refluxing ether to yield the corresponding benzyl alcohol (III). The controlled oxidation of (III) with pyridinium chlorochromate in dichloromethane affords 3-ethoxy-4-pentyloxybenazldehyde (IV), which is treated wtih NaCN and acetic acid - water giving 2-(3-ethoxy-4-pentyloxyphenyl)-2-hydroxyacetonitrile (V). Finally, this compound is cyclized with thiourea (VI) and HCl in 2-methoxyethanol. 2) The alkylation of ethyl-vanilline (VII) with c and K2CO3 in hot DMF gives aldehyde (IV), which by reaction with NaCH in methanol - HCl yields the cyanohydrine (V). The reaction of (V) with SOCl2 in refluxing CHCl3 affords 2-chloro-2-(3-ethoxy-5-pentyloxyphenyl)acetonitrile (VIII), which is finally cyclized with thiourea (VI) in ethylene glycol monomethyl ether - HCl at 110 C in refluxing ethanol - HCl. 3) The cyclization of 2-(3-ethoxy-4-pentyloxyphenyl)-2-hydroxyacetic acid (IX) with thiourea (VI) under acidic conditions gives 5-(3-ethoxy-4-pentyloxyphenyl)-2-iminothiazolidin-4-one (X), which is then hydrolyzed to the desired product.

1 Awata, T.; Maenaka, T.; Kawamatsu, Y. (Senju Pharmaceuticals Co., Ltd.); Ophthalmic topical agent for remedy of diseases of iris and ciliary body. EP 0170237; JP 1986043114; US 4602026 .
2 Kawamatsu, Y.; Yamamoto, Y. (Senju Pharmaceuticals Co., Ltd.; Takeda Chemical Industries, Ltd.); Thiazolidine derivs. and their production and use. EP 0033617 .
3 Imanishi, M.; Imamiya, E.; Kawamatsu, Y.; Hayashi, N.; Synthesis of 5-(3-ethoxy-4-pentyloxyphenyl)-2,4-[5-14C]thiazolidinedione ([14C]CT-112). J Takeda Res Lab 1983, 42, 3/4, 238-40.
4 Tawada, H.; Mizuno, K.; Meguro, K.; Sohda, T.; Imamiya, E.; Kawamatsu, Y.; Yamamoto, Y.; Studies on antidiabetic agents. III. 5-Arylthiazolidine-2,4-diones as potent aldose reductase inhibitors. Chem Pharm Bull 1982, 30, 10, 3601-16.
5 Prous, J.; Castaner, J.; CT-112. Drugs Fut 1991, 16, 10, 895.
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) 10398 2-Ethoxy-4-iodo-1-(pentyloxy)benzene; 2-Ethoxy-4-iodophenyl pentyl ether C13H19IO2 详情 详情
(II) 10399 3-Ethoxy-4-(pentyloxy)benzoic acid C14H20O4 详情 详情
(III) 10400 [3-Ethoxy-4-(pentyloxy)phenyl]methanol C14H22O3 详情 详情
(IV) 10401 3-Ethoxy-4-(pentyloxy)benzaldehyde C14H20O3 详情 详情
(V) 10402 2-[3-Ethoxy-4-(pentyloxy)phenyl]-2-hydroxyacetonitrile C15H21NO3 详情 详情
(VI) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(VII) 10404 Ethyl vanillin; 3-Ethoxy-4-hydroxybenzaldehyde 121-32-4 C9H10O3 详情 详情
(VIII) 10405 2-Chloro-2-[3-ethoxy-4-(pentyloxy)phenyl]acetonitrile C15H20ClNO2 详情 详情
(IX) 10406 2-[3-Ethoxy-4-(pentyloxy)phenyl]-2-hydroxyacetic acid C15H22O5 详情 详情
(X) 10407 5-[3-Ethoxy-4-(pentyloxy)phenyl]-2-imino-1,3-thiazolidin-4-one C16H22N2O3S 详情 详情
Extended Information