(E)-3-(2,4,5-trichlorophenyl)-2-propenoic acid -Drug Synthesis Database

【结构式】

【分子编号】46021

【品名】(E)-3-(2,4,5-trichlorophenyl)-2-propenoic acid

【CA登记号】

【分子式】C₉H₅Cl₃O₂

【分子量】251.4956

【元素组成】C 42.98% H 2% Cl 42.29% O 12.72%

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：(XVIII)

An improved procedure for the synthesis of intermediate (XVI) was further developed. Heck coupling of iodide (IX) with acrylic acid formed cinnamic acid (XVIII). This was converted to the corresponding acid chloride upon treatment with Vilsmeier reagent, and subsequent coupling with glycine tert-butyl ester gave amide (XIX). Selective chlorine displacement in (XIX) by means of the lithium salt of methyl mercaptoacetate, followed by in situ hydrolysis with LiOH, afforded acid (XVI).

参考文献中间体

合成目标

【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.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(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
(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
(XVII)	19139	acrylic acid	79-10-7	C₃H₄O₂	详情	详情
(XVIII)	46021	(E)-3-(2,4,5-trichlorophenyl)-2-propenoic acid		C₉H₅Cl₃O₂	详情	详情
(XIX)	46022	tert-butyl 2-[[(E)-3-(2,4,5-trichlorophenyl)-2-propenoyl]amino]acetate		C₁₅H₁₆Cl₃NO₃	详情	详情

Extended Information