ethyl 2-[1,1'-biphenyl]-4-ylacetate -Drug Synthesis Database

【结构式】

【分子编号】58171

【品名】ethyl 2-[1,1'-biphenyl]-4-ylacetate

【CA登记号】

【分子式】C₁₆H₁₆O₂

【分子量】240.30184

【元素组成】C 79.97% H 6.71% O 13.32%

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)

Esterification of (4'-biphenyl)acetic acid (I) with ethanol and p-toluenesulfonic acid provides the corresponding ethyl ester (II). Subsequent carbethoxylation of (II) with diethyl carbonate (III) under Claisen's condensation conditions furnishes the biphenylmalonate (IV). Cyclization of malonate (IV) with urea (V) in the presence of NaOEt leads to 5-(4'-biphenyl)barbituric acid (VI), which is further brominated to (VII) employing Br2 in aqueous HBr. The title compound is finally obtained by displacement of the 5-bromo barbituric acid (VII) with N-(4-nitrophenyl)piperazine (VIII) in refluxing MeOH.

参考文献中间体

合成目标

【1】 Bosies, E.; Esswein, A.; Grams, F.; Krell, H.-W.; Menta, E. (Roche Diagnostics GmbH); New barbituric acid derivs., processes for their production and pharmaceutical agents containing these cpds.. DE 19548624; EP 0869947; JP 2000505069; US 6110924; US 6472396; WO 9723465 .

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)	58170	2-[1,1'-biphenyl]-4-ylacetic acid		C₁₄H₁₂O₂	详情	详情
(II)	58171	ethyl 2-[1,1'-biphenyl]-4-ylacetate		C₁₆H₁₆O₂	详情	详情
(III)	17470	diethyl carbonate; diethylcarbonate	105-58-8	C₅H₁₀O₃	详情	详情
(IV)	58172	diethyl 2-[1,1'-biphenyl]-4-ylmalonate		C₁₉H₂₀O₄	详情	详情
(V)	19310	urea	57-13-6	CH₄N₂O	详情	详情
(VI)	58173	5-[1,1'-biphenyl]-4-yl-2,4,6(1H,3H,5H)-pyrimidinetrione		C₁₆H₁₂N₂O₃	详情	详情
(VII)	58174	5-[1,1'-biphenyl]-4-yl-5-bromo-2,4,6(1H,3H,5H)-pyrimidinetrione		C₁₆H₁₁BrN₂O₃	详情	详情
(VIII)	20299	1-(4-nitrophenyl)piperazine	6269-89-2	C₁₀H₁₃N₃O₂	详情	详情

Extended Information