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【结 构 式】

【分子编号】46018

【品名】(E)-3-[2,5-dichloro-4-[(2-methoxy-2-oxoethyl)sulfanyl]phenyl]-2-propenoic acid

【CA登记号】

【 分 子 式 】C12H10Cl2O4S

【 分 子 量 】321.1804

【元素组成】C 44.88% H 3.14% Cl 22.08% O 19.93% S 9.98%

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:(XIV)

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
Extended Information