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【结 构 式】

【分子编号】46024

【品名】(6R,7R)-7-([2-[(4-[(E)-3-[(carboxymethyl)amino]-3-oxo-1-propenyl]-2,5-dichlorophenyl)sulfanyl]acetyl]amino)-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

【CA登记号】

【 分 子 式 】C21H18Cl3N3O7S2

【 分 子 量 】594.88004

【元素组成】C 42.4% H 3.05% Cl 17.88% N 7.06% O 18.83% S 10.78%

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:(XXII)

Acylation of the cephem nucleus (XX) with the intermediate acid (XVI) via activation with either DCC or the Vilsmeier reagent provided amide (XXI). The ester groups of (XXI) were then cleaved with trifluoroacetic acid to give acid (XXII). Finally, condensation of (XXII) with pyridine thione (VII) furnished the title compound.

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.
3 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 .
2 Kim, O.; et al.; Discovery, synthesis and SAR of BMS-247243, a novel cephalosporin active against methicillin-resistant Staphylococcus aureus (MRSA) and susceptible Staphylococcus aureus (MSSA). 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1062.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 46012 4-[3-[2,6-dimethyl-4-thioxo-1(4H)-pyridinyl]propyl]-4-methylmorpholin-4-ium iodide C15H25IN2OS 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
(XX) 31135 benzhydryl (6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C21H19ClN2O3S 详情 详情
(XXI) 46023 benzhydryl (6R,7R)-7-[(2-[[4-((E)-3-[[2-(tert-butoxy)-2-oxoethyl]amino]-3-oxo-1-propenyl)-2,5-dichlorophenyl]sulfanyl]acetyl)amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C38H36Cl3N3O7S2 详情 详情
(XXII) 46024 (6R,7R)-7-([2-[(4-[(E)-3-[(carboxymethyl)amino]-3-oxo-1-propenyl]-2,5-dichlorophenyl)sulfanyl]acetyl]amino)-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C21H18Cl3N3O7S2 详情 详情
Extended Information