Felbinac ethyl, LJC-10253, LM-001, Traxam, Daitac, -Drug Synthesis Database

【结构式】

【药物名称】Felbinac ethyl, LJC-10253, LM-001, Traxam, Daitac

【化学名称】[1,1'-Biphenyl]-4-acetic acid ethyl ester

【CA登记号】14062-23-8

【分子式】C₁₆H₁₆O₂

【分子量】240.30472

【开发单位】Wyeth Pharmaceuticals (Originator)

【药理作用】Antiarthritic Drugs, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Non-Steroidal Antiinflammatory Drugs

合成路线1

Felbinac ethyl can be obtained in two different ways: 1) The Friedel-Craft's condensation of 2-chloro-2-(methylthio)acetic acid ethyl ester (I) with biphenyl (II) by means of SnCl4 in dichloromethane gives 2-(methylthio)-4-biphenylylacetic acid ethyl ester (III), which is reduced with Zn in acetic acid. 2) By condensation of diazoacetic acid ethyl ester (V) with 4-biphenylyldichloroborane (VI) in THF.

参考文献中间体

【1】 Purcell, T.A.; Rivron, L.; Zard, L. (Sanofi-Synthelabo ); Method for the preparation of 4-biphenylacetic acids. AU 8782884; EP 0272981; FR 2608206; JP 1988185975; US 4810723 .
【2】 Hooz, J.; Bridson, J.N.; Calzada, J.G.; Brown, H.C.; Midland, M.M.; Levy, A.B.; The reaction of alkyl- and aryldichloroboranes with ethyl diazoacetate at low temperature. J Org Chem 1973, 38, 14, 2574-76.
【3】 Prous, J.; Castaner, J.; LM-001. Drugs Fut 1990, 15, 11, 1077.

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)	31202	1,1'-biphenyl	92-52-4	C₁₂H₁₀	详情	详情
(II)	21726	ethyl 2-chloro-2-(methylsulfanyl)acetate		C₅H₉ClO₂S	详情	详情
(III)	31203	ethyl 2-[1,1'-biphenyl]-4-yl-2-(methylsulfanyl)acetate		C₁₇H₁₈O₂S	详情	详情
(IV)	31204	4-(dichloroboryl)-1,1'-biphenyl		C₁₂H₉BCl₂	详情	详情
(V)	31205	2-Diazoacetic acid ethyl ester		C₄H₆N₂O₂	详情	详情

Extended Information