tert-butyl 1-(hydroxymethyl)pentadecylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】51344

【品名】tert-butyl 1-(hydroxymethyl)pentadecylcarbamate

【CA登记号】

【分子式】C₂₁H₄₃NO₃

【分子量】357.57736

【元素组成】C 70.54% H 12.12% N 3.92% O 13.42%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

N-Boc-2-Aminohexadecanoic acid (I) was reduced to the Boc-aminoalcohol (III) via conversion to the mixed anhydride (II), which was subsequently reduced with NaBH4. Alcohol (III) was protected as the benzyl ether (IV) by alkylation with benzyl chloride in the presence of NaH. After acid deprotection of the N-Boc group of (IV), the resultant primary amine (V) was monoalkylated with ethyl bromide under controlled conditions to afford (VI). Finally, hydrogenolysis of the benzyl ether function of (VI) over Pd/C furnished the title amino alcohol.

参考文献中间体

合成目标

【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.
【2】 Alves, M.; del Olmo, E.; Ubeda, A.; López, J.L.; San Feliciano, A.; Lucas, R.; Payá, M.; Synthesis and enzyme inhibitory activities of a series of lipidic diamine and aminoalcohol derivatives on cytosolic and secretory phospholipases A2. Bioorg Med Chem Lett 2000, 10, 3, 285.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	51342	2-[(tert-butoxycarbonyl)amino]hexadecanoic acid	C₂₁H₄₁NO₄	详情	详情
(II)	51343		C₂₄H₄₅NO₆	详情	详情
(III)	51344	tert-butyl 1-(hydroxymethyl)pentadecylcarbamate	C₂₁H₄₃NO₃	详情	详情
(IV)	51345	tert-butyl 1-[(benzyloxy)methyl]pentadecylcarbamate	C₂₈H₄₉NO₃	详情	详情
(V)	51346	1-(benzyloxy)-2-hexadecanamine; 1-[(benzyloxy)methyl]pentadecylamine	C₂₃H₄₁NO	详情	详情
(VI)	51347	1-(benzyloxy)-N-ethyl-2-hexadecanamine; N-[1-[(benzyloxy)methyl]pentadecyl]-N-ethylamine	C₂₅H₄₅NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

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.

参考文献中间体

合成目标

【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