(E)-N-((1S)-4-amino-1-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-4-oxobutyl)-3-(4-nitrophenyl)-2-propenamide -Drug Synthesis Database

【结构式】

【分子编号】34549

【品名】(E)-N-((1S)-4-amino-1-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-4-oxobutyl)-3-(4-nitrophenyl)-2-propenamide

【CA登记号】

【分子式】C₁₈H₁₈N₄O₈

【分子量】418.36308

【元素组成】C 51.68% H 4.34% N 13.39% O 30.59%

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)

4-Nitrocinnamic acid (I) was activated as the succinimidyl ester (II) upon treatment with N-hydroxysuccinimide (NHS) and dicyclohexylcarbodiimide (DCC). Subsequent coupling of (II) with L-glutamine (III) afforded the N-acyl glutamine (IV). A second reaction of (IV) with NHS and DCC produced the active ester (V). Finally, thermal cyclization of (V), with concomitant racemization, led to the desired 2,6-piperidinedione.

参考文献中间体

合成目标

【1】 Hendry, L.B.; Design of drugs involving receptor-ligand-DNA interactions. WO 9514791 .
【2】 Hendry, L.B.; Computer-based design and screening of molecules using DNA interactions. US 5888741 .

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)	34546	(E)-3-(4-nitrophenyl)-2-propenoic acid	619-89-6	C₉H₇NO₄	详情	详情
(II)	34547	1-[[(E)-3-(4-nitrophenyl)-2-propenoyl]oxy]-2,5-pyrrolidinedione		C₁₃H₁₀N₂O₆	详情	详情
(III)	24948	L-glutamine	56-85-9	C₅H₁₀N₂O₃	详情	详情
(IV)	34548	(2S)-5-amino-2-[[(E)-3-(4-nitrophenyl)-2-propenoyl]amino]-5-oxopentanoic acid		C₁₄H₁₅N₃O₆	详情	详情
(V)	34549	(E)-N-((1S)-4-amino-1-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-4-oxobutyl)-3-(4-nitrophenyl)-2-propenamide		C₁₈H₁₈N₄O₈	详情	详情

Extended Information