(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】16914

【品名】(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate

【CA登记号】

【分子式】C₁₅H₂₀N₂O₆

【分子量】324.33368

【元素组成】C 55.55% H 6.22% N 8.64% O 29.6%

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：(XIII)

2) The hydrolysis of 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylic acid ethyl ester (VI) with LiOH in water gives the corresponding free acid (XII), which is esterified with the chloromethyldioxole (X) by means of diisopropylethylamine (DIEA) yielding the expected ester (XIII). Finally, this compound is condensed with 5-[4-'(bromomethyl)biphenyl-2-yl]-1-(triphenylmethyl)tetrazole (VII) by means of potassium carbonate in DMA to afford the protected CS-866 (XI) already obtained.

参考文献中间体

合成目标

【1】 Graul, A.; Leeson, P.; Castañer, J.; CS-866. Drugs Fut 1997, 22, 11, 1205.
【2】 Yanagisawa, H.; Shimoji, Y.; Fujimoto, K.; Kanazaki, T.; Anemiya, Y.; Koike, H.; Sada, T. (Sankyo Co., Ltd.); Angiotensin II antagonist 1-biphenylmethylimidazole cpds. and their therapeutic use. EP 0503785; EP 0545912; JP 1993078328; US 5616599 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	16907	ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate		C₁₂H₂₀N₂O₃	详情	详情
(VII)	15538	5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-trityl-2H-1,2,3,4-tetraazole	124750-51-2	C₃₃H₂₅BrN₄	详情	详情
(X)	16911	4-(chloromethyl)-5-methyl-1,3-dioxol-2-one		C₅H₅ClO₃	详情	详情
(XI)	16912	(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylate		C₄₈H₄₄N₆O₆	详情	详情
(XII)	16913	4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylic acid		C₁₀H₁₆N₂O₃	详情	详情
(XIII)	16914	(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate		C₁₅H₂₀N₂O₆	详情	详情

Extended Information