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【结 构 式】

【分子编号】16487

【品名】4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanone

【CA登记号】

【 分 子 式 】C13H13ClN2O

【 分 子 量 】248.7118

【元素组成】C 62.78% H 5.27% Cl 14.25% N 11.26% O 6.43%

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:(VII)

Reaction of the Grignard reagent derived from 4-chlorobenzyl bromide (I) with allyl bromide (II) gives 4-(4-chlorophenyl)but-1-ene (III), which is epoxidized with peracetic acid in dichloromethane to yield 4-(4-chlorophenyl)-1,2-epoxybutane (IV). Opening of (IV) with the anion of imidazole (V) gives 1-[4-(4-chlorophenyl)-2-hydroxybutyl]imidazole (VI), which is oxidized under Swern conditions to 4-(4-chlorophenyl)-1-(1-imidazolyl)-2-butanone (VII). Ketone (VII) is then reacted with (S)-solketal tosylate [(S)-1,2-O-isopropylideneglycerol-3-O-tosylate] (VIII) in the presence of p-toluenesulfonic acid in toluene to give a mixture of stereoisomers, and (2S,4S)-cis-2-[2-(4-chlorophenyl)ethyl]-2-(imidazol-1-ylmethyl)-4-(p-toluenesulfonyloxy)methyl-1,3-dioxolane (IX) is then separated by crystallization. Finally, (IX) is treated with 4-aminothiophenol (X) in the presence of potassium carbonate in acetone.

1 Dyson, N.H.; Gardner, J.O.; Prince, A.; Kertesz, D.J. (Syntex (USA), Inc.); Process for preparing 1,3-dioxolane derivs. JP 1995508002; US 5208331 .
2 Walker, K.A.; Burton, P.M.; Swinney, D.C. (Syntex (USA), Inc.); 1,3-Dioxolane derivs. as cholesterol lowering agents. JP 1992308588; US 5158949 .
3 Walker, K.A.M.; Rotstein, D.M.; Kertesz, D.J.; et al.; Selective inhibition of mammalian lanosterol 14alpha-demethylase: A possible strategy for cholesterol lowering. J Med Chem 1993, 36, 15, 2235-7.
4 Prous, J.; Mealy, N.; Castañer, J.; RS-21607-197. Drugs Fut 1994, 19, 2, 125.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 16481 1-(bromomethyl)-4-chlorobenzene 622-95-7 C7H6BrCl 详情 详情
(II) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(III) 16483 1-(3-butenyl)-4-chlorobenzene C10H11Cl 详情 详情
(IV) 16484 2-(4-chlorophenethyl)oxirane C10H11ClO 详情 详情
(V) 10255 Imidazole; 1H-Imidazole 288-32-4 C3H4N2 详情 详情
(VI) 16486 4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanol C13H15ClN2O 详情 详情
(VII) 16487 4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanone C13H13ClN2O 详情 详情
(VIII) 16488 (2S)-2,3-dihydroxypropyl 4-methylbenzenesulfonate C10H14O5S 详情 详情
(IX) 16489 [(2S,4S)-2-(4-chlorophenethyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate C23H25ClN2O5S 详情 详情
(X) 16490 4-aminophenylhydrosulfide; 4-aminothiophenol; 4-aminobenzenethiol 1193-02-8 C6H7NS 详情 详情
Extended Information