benzyl 2-(ditetradecylamino)-2-oxoethylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】17767

【品名】benzyl 2-(ditetradecylamino)-2-oxoethylcarbamate

【CA登记号】

【分子式】C₃₈H₆₈N₂O₃

【分子量】600.9696

【元素组成】C 75.95% H 11.4% N 4.66% O 7.99%

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：(IV)

Benzyloxycarbonylglycine (I) was coupled with N-hydroxysuccinimide in the presence of dicyclohexylcarbodiimide (DCC), and the resulting succinimidyl active ester (II) was condensed with dimiristylamine (III) to afford amide (IV). The benzyloxycarbonyl group was then removed by hydrogenolysis in the presence of palladium on carbon to yield amine (V). Coupling of this amine with Boc-protected L-arginine (VI) in the presence of diisopropylcarbodiimide (DIC) gave dipeptide (VII). Finally, partial deprotection of Boc groups with hydrochloric acid in dioxane provided the title compound.

参考文献中间体

合成目标

【1】 Lewis, J.G.; et al.; A serum-resistant cytofectin for cellular delivery of antisense oligodeoxynucleotides and plasmid DNA. Proc Natl Acad Sci USA 1996, 93, 8, 3177.
【2】 Deprince, R.B.; Facchine, K.L.; Lewis, G.S.; Lewis, J.G.; Lin, K.-Y.; Matteucci, M.D.; Mook, R.A. Jr.; Wagner, R.W. (Gilead Sciences Inc.; Glaxo Wellcome plc); Cationic lipids for delivery of nucleic acids to cells. WO 9601841 .

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)	17764	N-Carbobenzyloxyglycine; 2-[[(benzyloxy)carbonyl]amino]acetic acid	1138-80-3	C₁₀H₁₁NO₄	详情	详情
(II)	17765	benzyl 2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethylcarbamate; Z-glycine N-succinimidyl ester	2899-60-7	C₁₄H₁₄N₂O₆	详情	详情
(III)	17766	DITETRADECYLAMINE; N-tetradecyl-1-tetradecanamine; N,N-ditetradecylamine	17361-44-3	C₂₈H₅₉N	详情	详情
(IV)	17767	benzyl 2-(ditetradecylamino)-2-oxoethylcarbamate		C₃₈H₆₈N₂O₃	详情	详情
(V)	17768	2-amino-N,N-ditetradecylacetamide		C₃₀H₆₂N₂O	详情	详情
(VI)	17769	(2S)-2-[(tert-butoxycarbonyl)amino]-5-[(tert-butoxycarbonyl)[imino(methylamino)methyl]amino]pentanoic acid		C₁₇H₃₂N₄O₆	详情	详情
(VII)	17770	tert-butyl (4S)-4-[(tert-butoxycarbonyl)amino]-5-[[2-(ditetradecylamino)-2-oxoethyl]amino]-5-oxopentyl[[(tert-butoxycarbonyl)amino](imino)methyl]carbamate		C₅₁H₉₈N₆O₈	详情	详情

Extended Information