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【结 构 式】

【分子编号】69006

【品名】ethyl 5-(tert-butyl)-1H-imidazole-4-carboxylate

【CA登记号】 

【 分 子 式 】C10H16N2O2

【 分 子 量 】196.24932

【元素组成】C 61.2% H 8.22% N 14.27% O 16.31%

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:(X)

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 .

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