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【结 构 式】 
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【分子编号】46017 【品名】tert-butyl (E)-3-[2,5-dichloro-4-[(2-methoxy-2-oxoethyl)sulfanyl]phenyl]-2-propenoate 【CA登记号】 |
【 分 子 式 】C16H18Cl2O4S 【 分 子 量 】377.28792 【元素组成】C 50.94% H 4.81% Cl 18.79% O 16.96% S 8.5% |
合成路线1
该中间体在本合成路线中的序号：(XIII)The iodination of trichloroaniline (VIII) via diazotization produced iodide (IX). Subsequent Heck reaction of iodide (IX) with tert-butyl acrylate (X) furnished tert-butyl trichlorocinnamate (XI), which was condensed with the sodium salt of methyl mercaptoacetate (XII), yielding thioether (XIII). After acid cleavage of the tert-butyl ester of (XIII), the resulting carboxylic acid (XIV) was coupled with glycine tert-butyl ester via activation as the corresponding N-hydroxysuccinimidyl ester. Then, saponification of the methyl ester group of (XV) afforded the intermediate acid (XVI).
| 【1】 Singh, J.; et al.; A practical synthesis of an anti-methicillin resistant Staphylococcus aureus cephalosporin BMS-247243. Org Process Res Dev 2000, 4, 6, 488. |
| 【2】 Springer, D.M.; Luh, B.Y.; D'Andrea, S.V.; Hudyma, T.W.; Kim, O.K. (Bristol-Myers Squibb Co.); Cephalosporin derivs.. EP 0966472; WO 9823621 . |
| 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) | 46013 | 2,4,5-trichlorophenylamine; 2,4,5-trichloroaniline | 636-30-6 | C6H4Cl3N | 详情 | 详情 |
| (IX) | 46014 | 1-Iodo-2,4,5-trichlorobenzene; 2,4,5-Trichloroiodobenzene; 1,2,4-trichloro-5-iodobenzene | 7145-82-6 | C6H2Cl3I | 详情 | 详情 |
| (X) | 12760 | tert-butyl acrylate | 1663-39-4 | C7H12O2 | 详情 | 详情 |
| (XI) | 46015 | tert-butyl (E)-3-(2,4,5-trichlorophenyl)-2-propenoate | C13H13Cl3O2 | 详情 | 详情 | |
| (XII) | 46016 | sodium 2-methoxy-2-oxo-1-ethanethiolate | C3H5NaO2S | 详情 | 详情 | |
| (XIII) | 46017 | tert-butyl (E)-3-[2,5-dichloro-4-[(2-methoxy-2-oxoethyl)sulfanyl]phenyl]-2-propenoate | C16H18Cl2O4S | 详情 | 详情 | |
| (XIV) | 46018 | (E)-3-[2,5-dichloro-4-[(2-methoxy-2-oxoethyl)sulfanyl]phenyl]-2-propenoic acid | C12H10Cl2O4S | 详情 | 详情 | |
| (XV) | 46019 | methyl 2-[[4-((E)-3-[[2-(tert-butoxy)-2-oxoethyl]amino]-3-oxo-1-propenyl)-2,5-dichlorophenyl]sulfanyl]acetate | C18H21Cl2NO5S | 详情 | 详情 | |
| (XVI) | 46020 | 2-[[4-((E)-3-[[2-(tert-butoxy)-2-oxoethyl]amino]-3-oxo-1-propenyl)-2,5-dichlorophenyl]sulfanyl]acetic acid | C17H19Cl2NO5S | 详情 | 详情 |