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【结 构 式】 
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【分子编号】59151 【品名】5-(2,5-Dioxopyrrolidin-1-yl)-4-oxopentanoic acid 【CA登记号】 |
【 分 子 式 】C9H11NO5 【 分 子 量 】213.19008 【元素组成】C 50.71% H 5.2% N 6.57% O 37.52% |
合成路线1
该中间体在本合成路线中的序号：(XIX)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.
| 【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 |