1-(3-nitrophenyl)-5-oxo-3-pyrrolidinecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】57782

【品名】1-(3-nitrophenyl)-5-oxo-3-pyrrolidinecarboxylic acid

【CA登记号】

【分子式】C₁₁H₁₀N₂O₅

【分子量】250.21088

【元素组成】C 52.8% H 4.03% N 11.2% O 31.97%

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：(III)

Cyclization of itaconic acid (I) with 3-nitroaniline (II) at 100 C gives rise to 1-(3-nitrophenyl)-5-oxopyrrolidine-3-carboxylic acid (III). Subsequent condensation of acid (III) with methyl 3-amino-3-(3,5-dichlorophenyl)propanoate (IV) in the presence of EDC and HOAt yields amide (V). Reduction of the nitro group of (V) to the corresponding amine (VI) is effected by means of Zn and HOAc. Amine (VI) is then condensed with the cyclic thiourea (VII) employing HgCl2 to furnish the di-Boc-protected guanidine (VIII). Saponification of the methyl ester function of (VIII) then gives acid (IX). The N-Boc groups of (IX) are finally removed by treatment with trifluoroacetic acid to furnish the title compound.

参考文献中间体

合成目标

【1】 Dominguez, C.; Chen, G.; Liu, L.; Liu, Q.; Han, N.; Xi, N.; Xu, S.; Huang, Q.; Siegmund, A.; Handley, M.; Kiselyov, A.S. (Amgen Inc.); 1-(Aminophenyl)-2-pyrrolidones as integrin inhibitors. EP 1240158; US 2002019402; WO 0144230 .

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)	27493	2-methylenesuccinic acid	97-65-4	C₅H₆O₄	详情	详情
(II)	57781	1-Amino-3-Nitrobenzene; 3-Nitroaniline; m-Nitroaniline	99-09-2	C₆H₆N₂O₂	详情	详情
(III)	57782	1-(3-nitrophenyl)-5-oxo-3-pyrrolidinecarboxylic acid		C₁₁H₁₀N₂O₅	详情	详情
(IV)	57783	methyl 3-amino-3-(3,5-dichlorophenyl)propanoate		C₁₀H₁₁Cl₂NO₂	详情	详情
(V)	57784	methyl 3-(3,5-dichlorophenyl)-3-({[1-(3-nitrophenyl)-5-oxo-3-pyrrolidinyl]carbonyl}amino)propanoate		C₂₁H₁₉Cl₂N₃O₆	详情	详情
(VI)	57785	methyl 3-({[1-(3-aminophenyl)-5-oxo-3-pyrrolidinyl]carbonyl}amino)-3-(3,5-dichlorophenyl)propanoate		C₂₁H₂₁Cl₂N₃O₄	详情	详情
(VII)	57786	di(tert-butyl) 2-thioxodihydro-1,3(2H,4H)-pyrimidinedicarboxylate		C₁₄H₂₄N₂O₄S	详情	详情
(VIII)	57787	di(tert-butyl) 2-({3-[4-({[1-(3,5-dichlorophenyl)-3-methoxy-3-oxopropyl]amino}carbonyl)-2-oxo-1-pyrrolidinyl]phenyl}imino)dihydro-1,3(2H,4H)-pyrimidinedicarboxylate		C₃₅H₄₃Cl₂N₅O₈	详情	详情
(IX)	57788	N-{[1-(3-{[1,3-bis(tert-butoxycarbonyl)tetrahydro-2(1H)-pyrimidinylidene]amino}phenyl)-5-oxo-3-pyrrolidinyl]carbonyl}-3-(3,5-dichlorophenyl)-beta-alanine		C₃₄H₄₁Cl₂N₅O₈	详情	详情

Extended Information