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【结 构 式】 
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【分子编号】31624 【品名】dimethyl 2-[2-(3,5-difluorophenyl)acetyl]-2-[2-[4-(methylsulfonyl)phenyl]-2-oxoethyl]malonate 【CA登记号】 |
【 分 子 式 】C22H20F2O8S 【 分 子 量 】482.4588064 【元素组成】C 54.77% H 4.18% F 7.88% O 26.53% S 6.65% |
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：(XII)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.
| 【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