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【结 构 式】 
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【分子编号】27236 【品名】2-(benzoylamino)acetic acid 【CA登记号】495-69-2 |
【 分 子 式 】C9H9NO3 【 分 子 量 】179.1754 【元素组成】C 60.33% H 5.06% N 7.82% O 26.79% |
合成路线1
该中间体在本合成路线中的序号：(LXI)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 |
合成路线2
该中间体在本合成路线中的序号：(II)Condensation of benzaldehyde (I) with hippuric acid (II) in the presence of NaOAc in boiling Ac2O furnished oxazolone (III). The title compound was then obtained by ring opening of (III) with piperidine (IV) in chloroform at 0 C, followed by chlorination with Cl2 gas.
| 【1】 Conway, S.C.; Perni, R.B. (Avid Corp.); 2-Benzoylamino-3-phenylpropenamide derivs. and methods of using the same. WO 9833501 . |