ethyl 2-chloro-4,4-dimethyl-3-oxopentanoate -Drug Synthesis Database

【结构式】

【分子编号】69005

【品名】ethyl 2-chloro-4,4-dimethyl-3-oxopentanoate

【CA登记号】　

【分子式】C₉H₁₅ClO₃

【分子量】206.669

【元素组成】C 52.31% H 7.32% Cl 17.15% O 23.22%

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：(VIII)

The intermediate 5-tert-butylimidazole-4-carbaldehyde (III) is prepared by reaction of ethyl pivaloyl acetate (VII) with sulfuryl chloride in chloroform to provide the 2-chloro derivative (VIII), which is cyclized with formamide (IX) in the presence of a trace of water in a sealed tube at 150 oC, affording ethyl 5-tert-butylimidazole-4-carboxylate (X). Reduction of ester (X) with LiAlH4 in THF gives alcohol (XI), which is finally oxidized to the target carbaldehyde (III) using MnO2 in acetone .

参考文献中间体

合成目标

【1】 Hayashi, Y., Grodberg, J., Palladino, M. (Nereus Pharmaceuticals, Inc). Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins dehydrophenylahistins and analogs thereof. EP 1529044, JP 2006511534, WO 2004054498.
【2】 Palladino, M.A., Lloyd, G.K., Hayashi, Y., Nicholson, B. (Nereus Pharmaceuticals, Inc). Dehydrophenylahistins and analogs thereof and the synthesis of dehydrophenylahistins and analogs thereof. EP 1711487, JP 2007520565, WO 2005077940.
【3】 Palladino, M., Lloyd, G.K., Hayashi, Y. (Nereus Pharmaceuticals, Inc). Analogs of dehydrophenylahistins and their therapeutic use. EP 1926724, US 2007078138, WO 2007035841.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	69002	5-tert-butylimidazole-4-carbaldehyde;5-(1,1-dimethylethyl)-1H-Imidazole-4-carboxaldehyde;4-(1,1-dimethylethyl)-1H-Imidazole-5-carboxaldehyde	714273-83-3	C₈H₁₂N₂O	详情	详情
(VII)	69004	ethyl 4,4-dimethyl-3-oxopentanoate;Ethyl pivaloylacetate	17094-34-7	C₉H₁₆O₃	详情	详情
(VIII)	69005	ethyl 2-chloro-4,4-dimethyl-3-oxopentanoate		C₉H₁₅ClO₃	详情	详情
(IX)	16598	Formamide	75-12-7	CH₃NO	详情	详情
(X)	69006	ethyl 5-(tert-butyl)-1H-imidazole-4-carboxylate		C₁₀H₁₆N₂O₂	详情	详情
(XI)	69007	(5-(tert-butyl)-1H-imidazol-4-yl)methanol		C₈H₁₄N₂O	详情	详情

Extended Information