N-(3-amino-3-oxopropyl)-2-sulfanylbenzamide -Drug Synthesis Database

【结构式】

【分子编号】58513

【品名】N-(3-amino-3-oxopropyl)-2-sulfanylbenzamide

【CA登记号】

【分子式】C₁₀H₁₂N₂O₂S

【分子量】224.28356

【元素组成】C 53.55% H 5.39% N 12.49% O 14.27% S 14.3%

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：(V)

2,2'-Dithiosalicylic acid (I) is activated as the bis-succinimidyl ester (II) upon treatment with N-hydroxysuccinimide and DIC. Coupling of the active ester (II) with 3-aminopropionamide (III) gives rise to the corresponding dithiosalicylamide (IV). Reductive cleavage of the disulfide bond of (IV) using tris(2-carboxyethyl)phosphine (TCEP) affords thiol (V). The desired thiolcarbamate is then obtained by condensation of (V) with tert-butyl isocyanate in DMF.

参考文献中间体

合成目标

【1】 Goel, A.; et al.; Benzamide-based thiocarbamates: A new class of HIV-1 NCp7 inhibitors. Bioorg Med Chem Lett 2002, 12, 5, 767.

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)	20404	2-[(2-carboxyphenyl)disulfanyl]benzoic acid; 2,2'-Dithiodibenzoic acid	119-80-2	C₁₄H₁₀O₄S₂	详情	详情
(II)	58510	1-({2-[(2-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}phenyl)disulfanyl]benzoyl}oxy)-2,5-pyrrolidinedione		C₂₂H₁₆N₂O₈S₂	详情	详情
(III)	58511	3-aminopropanamide		C₃H₈N₂O	详情	详情
(IV)	58512	N-(3-amino-3-oxopropyl)-2-[(2-{[(3-amino-3-oxopropyl)amino]carbonyl}phenyl)disulfanyl]benzamide		C₂₀H₂₂N₄O₄S₂	详情	详情
(V)	58513	N-(3-amino-3-oxopropyl)-2-sulfanylbenzamide		C₁₀H₁₂N₂O₂S	详情	详情

Extended Information