dimethyl 3-(3,5-difluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-oxo-3-cyclopentene-1,1-dicarboxylate -Drug Synthesis Database

【结构式】

【分子编号】31625

【品名】dimethyl 3-(3,5-difluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-oxo-3-cyclopentene-1,1-dicarboxylate

【CA登记号】

【分子式】C₂₂H₁₈F₂O₇S

【分子量】464.4435264

【元素组成】C 56.89% H 3.91% F 8.18% O 24.11% S 6.9%

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：(XIII)

The alkylation of dimethyl malonate (IX) with 4-(methylsulfonyl)phenacyl bromide (VIII) by means of K2CO3 in hot acetone gives the substituted malonic ester (X), which is condensed with 2-(3,5-difluorophenyl)acetyl chloride (XI) by means of MgBr2 and pyridine in acetonitrile yielding the disubstituted malonic ester (XII). The cyclization of (XII) by means of triethylamine affords the cylopentenone dicarboxylic ester (XIII), which is finally decarboxylated with H2SO4 in hot acetic acid to provide the target compound.

参考文献中间体

合成目标

【1】 Grabowski, E.J.J.; Zhaol, D.L.; Prasit, P.; Xu, F.; Ouimet, N.; Tillyer, R.D.; Black, C.; Chen, C.Y.; Reider, P.J.; Efficient syntheses of 2-(3 ',5 '-difluorophenyl)-3-(4 '-methylsulfonylphenyl)-cyclopent-2-enone, a potent COX-2 inhibitor. Tetrahedron 1999, 55, 19, 6001.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	19624	(4R,5S,6S,7R)-4,7-dibenzyl-1,3-bis(3-iodobenzyl)-5,6-bis(methoxymethoxy)-1,3-diazepan-2-one		C₃₇H₄₀I₂N₂O₅	详情	详情
(IX)	19373	dimethyl malonate；Methyl malonate;Propanedioic acid dimethyl ester	108-59-8	C₅H₈O₄	详情	详情
(X)	31626	dimethyl 2-[2-[4-(methylsulfonyl)phenyl]-2-oxoethyl]malonate		C₁₄H₁₆O₇S	详情	详情
(XI)	28362	2-(3,5-difluorophenyl)acetyl chloride		C₈H₅ClF₂O	详情	详情
(XII)	31624	dimethyl 2-[2-(3,5-difluorophenyl)acetyl]-2-[2-[4-(methylsulfonyl)phenyl]-2-oxoethyl]malonate		C₂₂H₂₀F₂O₈S	详情	详情
(XIII)	31625	dimethyl 3-(3,5-difluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-oxo-3-cyclopentene-1,1-dicarboxylate		C₂₂H₁₈F₂O₇S	详情	详情

Extended Information