2,5-pyrrolidinedione -Drug Synthesis Database

【结构式】

【分子编号】22543

【品名】2,5-pyrrolidinedione

【CA登记号】123-56-8

【分子式】C₄H₅NO₂

【分子量】99.08924

【元素组成】C 48.49% H 5.09% N 14.14% O 32.29%

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：(I)

The alkylation of succinimide (I) with 1,2-dibromoethane (II) by means of K2CO3 in refluxing butanone gives N-(2-bromoethyl)succinimide (III), which is condensed with 4-hydroxythiophenol (IV) by means of K2CO3 in refluxing ethanol to afford 4-hydroxyphenyl 2-succinimidoethyl sulfide (V). Finally, this compound is esterified with 4-guanidinobenzoyl chloride in pyridine, and treated with methanesulfonic acid in methanol.

参考文献中间体

合成目标

【1】 Hishinuma, I.; Kawashima, H.; Kawata, T.; Miyamoto, K.; Miyazawa, S.; Nagakawa, J.; Nagaoka, J.; Nagaoka, N.; Shimomura, N.; Souda, S.; Ueda, N.; Wakabayashi, T.; Yamanaka, T. (Eisai Co., Ltd.); Guanidinobenzoic ester deriv., a process for preparing same and pharmaceutical compsns. containing same. EP 0229370; JP 1987155253; JP 1994298730; US 4801603; US 5075335 .
【2】 Prous, J.; Castaner, J.; E-3123. Drugs Fut 1988, 13, 7, 613.

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)	22543	2,5-pyrrolidinedione	123-56-8	C₄H₅NO₂	详情	详情
(II)	10252	1,2-Dibromoethane; Ethylene dibromide	106-93-4	C₂H₄Br₂	详情	详情
(III)	22545	1-(2-bromoethyl)-2,5-pyrrolidinedione		C₆H₈BrNO₂	详情	详情
(IV)	22546	4-sulfanylphenol	637-89-8	C₆H₆OS	详情	详情
(V)	22547	1-[2-[(4-hydroxyphenyl)sulfanyl]ethyl]-2,5-pyrrolidinedione		C₁₂H₁₃NO₃S	详情	详情
(VI)	22548	4-[[amino(imino)methyl]amino]benzoyl chloride		C₈H₈ClN₃O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVII)

Alternatively, the mono-methyl ester of succinic acid (XIII) was prepared by refluxing succinic anhydride (XII) with MeOH. Subsequent treatment of (XIII) with SOCl2 gave acid chloride (XIV). This was condensed with diazomethane to produce the diazo ketone (XV), which was further converted to the chloro ketone (XVI) by treatment with HCl. Condensation of chlorolevulinate (XVI) with succinimide (XVII) produced methyl delta-succinimidolevulinate (XVIII). Smooth acidic hydrolysis of the methyl ester group of (XVIII) led to the succinimido acid (XIX), which was further hydrolyzed to the succinamido acid (XX) under basic conditions. The title compound could be obtained by hydrolysis of either (XVIII), (XIX) or (XX) in refluxing 7N HCl.

参考文献中间体

合成目标

【1】 Neuberger, A.; Scott, J.J.; The synhtesis of delta-succinamidolaevulic acid and related compounds. J Chem Soc 1954, 1820.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XII)	11291	Dihydro-2,5-furandione; Succinic anhydride	108-30-5	C₄H₄O₃	详情	详情
(XIII)	55901	Methyl hydrogen succinate; Succinic acid monomethyl ester; Monomethyl succinate	3878-55-5	C₅H₈O₄	详情	详情
(XIV)	18060	4-Chloro-4-oxobutyric acid methyl ester; 3-Carbomethosypropionyl chloride; Methyl 4-chloro-4-oxobutanoate	1490-25-1	C₅H₇ClO₃	详情	详情
(XV)	59148			C₆H₈N₂O₃	详情	详情
(XVI)	59149	methyl 5-chloro-4-oxopentanoate		C₆H₉ClO₃	详情	详情
(XVII)	22543	2,5-pyrrolidinedione	123-56-8	C₄H₅NO₂	详情	详情
(XVIII)	59150	methyl 5-(2,5-dioxo-1-pyrrolidinyl)-4-oxopentanoate		C₁₀H₁₃NO₅	详情	详情
(XIX)	59151	5-(2,5-Dioxopyrrolidin-1-yl)-4-oxopentanoic acid		C₉H₁₁NO₅	详情	详情
(XX)	59152	5-[(3-carboxypropanoyl)amino]-4-oxopentanoic acid		C₉H₁₃NO₆	详情	详情

Extended Information