【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 |