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【结 构 式】

【药物名称】

【化学名称】2-(tert-Butoxycarbonyl-L-leucyl-L-leucyl)-1H-imidazole

【CA登记号】

【 分 子 式 】C20H34N4O4

【 分 子 量 】394.51838

【开发单位】Cephalon (Originator)

【药理作用】Cerebrovascular Diseases, Treatment of, Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of

合成路线1

The condensation of tert-butoxycarbonyl-L-leucinal (I) with 1-benzylimidazole (II) by means of BuLi in THF gives 1-benzyl-2-[2(S)-(tert-butoxycarbonylamino)-1-hydroxy-4-methylpentyl]imidazole (III), which is hydrolyzed with HCl in dioxane yielding 2-(2(S)-amino)-1-hydroxy-4-methylpentyl]-2-benzylimidazole (IV). The condensation of (IV) with tert-butoxycarbonyl-L-leucine (V) by means of dicyclohexylcarbodiimide (DCC) and hydroxybenzotriazole (HOBT) in TFA/dichloromethane affords the protected seudo-dipeptide (VI), which is debenzylated with H2 over Pd/C giving the expected seudo-peptide (VII): Finally, this compound is oxidizad with the Dess-Martin oxidant.

1 Tao, M.; et al.; Inhibition of calpain by peptidyl heterocycles. Bioorg Med Chem Lett 1996, 6, 24, 3009.
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) 27058 tert-butyl (1S)-1-formyl-3-methylbutylcarbamate C11H21NO3 详情 详情
(II) 27059 1-benzyl-1H-imidazole 4238-71-5 C10H10N2 详情 详情
(III) 27060 tert-butyl (1S)-1-[(1-benzyl-1H-imidazol-2-yl)(hydroxy)methyl]-3-methylbutylcarbamate C21H31N3O3 详情 详情
(IV) 27061 (2S)-2-amino-1-(1-benzyl-1H-imidazol-2-yl)-4-methyl-1-pentanol C16H23N3O 详情 详情
(V) 23663 (2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid;N-Boc-L-leucine C11H21NO4 详情 详情
(VI) 27062 tert-butyl (1S)-1-[([(1S)-1-[(1-benzyl-1H-imidazol-2-yl)(hydroxy)methyl]-3-methylbutyl]amino)carbonyl]-3-methylbutylcarbamate C27H42N4O4 详情 详情
(VII) 27063 tert-butyl (1S)-1-[([(1S)-1-[hydroxy(1H-imidazol-2-yl)methyl]-3-methylbutyl]amino)carbonyl]-3-methylbutylcarbamate C20H36N4O4 详情 详情
Extended Information