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【结 构 式】

【药物名称】

【化学名称】N-[1-(Diethylaminomethyl)pentadecyl]carbamic acid tert-butyl ester

【CA登记号】

【 分 子 式 】C25H52N2O2

【 分 子 量 】412.70539

【开发单位】Univ. Nacl. Asunci髇 (Originator), Universidad de Salamanca (Originator)

【药理作用】ANTIINFECTIVE THERAPY, Antileishmanials, Treatment of Protozoal Diseases

合成路线1

The reaction of 2-(tert-butoxycarbonylamino)hexadecanoic acid (I) with ethyl chloroformate (II) and NMM in THF gives the mixed anhydride (III), which is reduced by means of NaBH4 in methanol to yield the corresponding hexadecanol (IV). The reaction of (IV) with MsCl and TEA affords the mesylate (V), which is treated with sodium azide in DMF to provide the azido derivative (VI). The reduction of (VI) with H2 over Pd/C in chloroform gives the corresponding amine (VII), which is finally alkylated with ethyl bromide and TEA in DMF to yield the target tertiary amine.

1 del Olmo, E.; Alves, M.; Lopez, J.L.; Inchaustti, A.; Yaluff, G.; Rojas de Arias, A.; San Feliciano, A.; Leishmanicidal activity of some aliphatic diamines and amino-alcohols. Bioorg Med Chem Lett 2002, 12, 4, 659.
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) 51342 2-[(tert-butoxycarbonyl)amino]hexadecanoic acid C21H41NO4 详情 详情
(II) 16993 methyl chlorocarbonate;Carbonochloridic acid methyl ester;[(chlorocarbonyl)oxy]methane;methyl chloroformate 79-22-1 C2H3ClO2 详情 详情
(III) 51343   C24H45NO6 详情 详情
(IV) 51344 tert-butyl 1-(hydroxymethyl)pentadecylcarbamate C21H43NO3 详情 详情
(V) 63167 2-[(tert-butoxycarbonyl)amino]hexadecyl methanesulfonate C22H45NO5S 详情 详情
(VI) 63168 tert-butyl 1-(azidomethyl)pentadecylcarbamate C21H42N4O2 详情 详情
(VII) 63169 tert-butyl 1-(aminomethyl)pentadecylcarbamate C21H44N2O2 详情 详情
Extended Information