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【结 构 式】

【分子编号】15303

【品名】2-[4-(ethoxycarbonyl)-3-hydroxyphenyl]acetic acid

【CA登记号】

【 分 子 式 】C11H12O5

【 分 子 量 】224.21328

【元素组成】C 58.93% H 5.39% O 35.68%

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:(IV)

1) The condensation of 3-methyl-1-[2-(1-piperidinyl)phenyl)butylamine (I) with 2-[3-ethoxy-4-(ethoxycarbonyl)phenyl]acetic acid (II) by means of triphenylphosphine, triethylamine and CCl4 gives the corresponding amide-ester (III), which is then hydrolyzed with NaOH in ethanol/water to the racemic repaglinide. 2) The condensation of amine (I) with 2-[4-(ethoxycarbonyl)-3-hydroxyphenyl]acetic acid (IV) by means of triphenylphosphine as before yields the corresponding amide-ester (V), which is then submitted to ethoxylation with NaH and ethyl bromide in DMF to afford the racemic amide-ester (III), already obtained.

1 Graul, A.; Castaner, J.; Repaglinide. Drugs Fut 1996, 21, 7, 694.
2 Grell, W. (Dr. Karl Thomae GmbH); New solid forms of 2-ethoxy-4-[N-[1-(2-piperidino-phenyl)-3-methyl-1-butyl] aminocarbonylmethyl]benzoic acid, medicines containing them and process for their preparation. AU 8659139; DE 3522604; EP 0207331; ES 8802145; JP 1987000474 .
3 Kwak, J.H.; Jeong, Y.N.; Oh, J.I. (LG Chem Ltd.); Novel quinoline carboxylic acid derivs. having 7-(4-amino-methyl-3-oxime)pyrrolidine substituents and processes for their preparation. CA 2151890; EP 0688772; JP 1996041050; US 5633262; US 5698570; US 5776944 .
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) 15300 3-methyl-1-(2-piperidinophenyl)-1-butanamine; 3-methyl-1-(2-piperidinophenyl)butylamine C16H26N2 详情 详情
(II) 15301 2-[3-ethoxy-4-(ethoxycarbonyl)phenyl]acetic acid C13H16O5 详情 详情
(III) 15302 ethyl 2-ethoxy-4-(2-[[3-methyl-1-(2-piperidinophenyl)butyl]amino]-2-oxoethyl)benzoate C29H40N2O4 详情 详情
(IV) 15303 2-[4-(ethoxycarbonyl)-3-hydroxyphenyl]acetic acid C11H12O5 详情 详情
(V) 15304 ethyl 2-hydroxy-4-(2-[[3-methyl-1-(2-piperidinophenyl)butyl]amino]-2-oxoethyl)benzoate C27H36N2O4 详情 详情
Extended Information