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【结 构 式】 
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【分子编号】59187 【品名】Ethyl hippurate 【CA登记号】 |
【 分 子 式 】C11H13NO3 【 分 子 量 】207.22916 【元素组成】C 63.76% H 6.32% N 6.76% O 23.16% |
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：(LXIII)The acylation of hippuric acid (LXI) with methyl succinyl chloride (XIV) in cold 4-picoline gave rise to the acyl oxazolinone (LXII). Subsequent acidic hydrolysis of (LXII) provided delta-aminolevulinic acid. In a related strategy, the lithio-dianion of ethyl hippurate (LXIII) was acylated with succinic anhydride (XII) producing the 2-amino-3-oxoadipic acid derivative (LXIV). Further hydrolysis and decarboxylation of (LXIV) under acidic conditions furnished the target compound.
| 【1】 Sidebottom, P.J.; Evans, D.A.; A simple route to alpha-aminoketones and related derivatives by dianion acylation reactions; an improved preparation of delta-aminolevulinic acid. J Chem Soc Chem Commun 1978, 753. |
| 【2】 Aronova, N.I.; Makhova, N.N.; Zavyalov, S.I.; Volkenshtein, J.B.; Kunitskaya, G.M.; Method of producing delta-aminolevulinic acid hydrochloride. US 3846490 . |
| 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 |
| (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 |
| (LXI) | 27236 | 2-(benzoylamino)acetic acid | 495-69-2 | C9H9NO3 | 详情 | 详情 |
| (LXII) | 59186 | methyl 4-oxo-4-(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)butanoate | C14H13NO5 | 详情 | 详情 | |
| (LXIII) | 59187 | Ethyl hippurate | C11H13NO3 | 详情 | 详情 | |
| (LXIV) | 59188 | 5-(benzoylamino)-6-ethoxy-4,6-dioxohexanoic acid | C15H17NO6 | 详情 | 详情 |
Extended Information