|
【结 构 式】 
|
【分子编号】40150 【品名】(1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carboxylic acid 【CA登记号】 |
【 分 子 式 】C24H32O5 【 分 子 量 】400.51508 【元素组成】C 71.97% H 8.05% O 19.97% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of maleopimaric acid (I) with aqueous ammonia and heating at 170 C gives maleopimarimide (II), which by reaction with oxalyl chloride in benzene is converted into the corresponding acyl chloride (III). The reaction of (III) with morpholine (A) in benzene yields maleopimarimidyl morpholide (IV), which is finally condensed with ethanolamine (B) in refluxing methanol.
| 【1】 Danswan, G.W.; Ramm, P.J.; Matharu, S.; Taylor, J.B.; hepatoprotective agents. II. Maleopimaridyl morpholides. Arzneim-Forsch Drug Res 1976, 26, 12, 2190-92. |
| 【2】 Thorpe, P.; Castaner, J.; RU 18492. Drugs Fut 1977, 2, 9, 623. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 10259 | Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol | 141-43-5 | C2H7NO | 详情 | 详情 |
| (A) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |
| (I) | 40150 | (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carboxylic acid | C24H32O5 | 详情 | 详情 | |
| (II) | 40151 | (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-azapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carboxylic acid | C24H33NO4 | 详情 | 详情 | |
| (III) | 40152 | (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-azapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carbonyl chloride | C24H32ClNO3 | 详情 | 详情 | |
| (IV) | 40153 | (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-5-(4-morpholinylcarbonyl)-15-azapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-14,16-dione | C28H40N2O4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The reaction of maleopimaric acid (I) with SOCl2 in benzene produces the corresponding acyl chloride (V), which is then condensed with morpholine (A) by means of Et3N in benzene yielding maleopimaryl morpholide (VI). Finally, (VI) is condensed with ethanolamine (B) in refluxing ethanol.
| 【1】 Taylor, J.B.; et al. (Aventis Pharma SA); Novel derivatives of maleopimaric acid. DE 2351343; FR 2202691; GB 1417996; JP 49093356; US 3998823 . |
| 【2】 Thorpe, P.; Castaner, J.; RU 18492. Drugs Fut 1977, 2, 9, 623. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 10259 | Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol | 141-43-5 | C2H7NO | 详情 | 详情 |
| (A) | 10388 | Morpholine | 110-91-8 | C4H9NO | 详情 | 详情 |
| (I) | 40150 | (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carboxylic acid | C24H32O5 | 详情 | 详情 | |
| (V) | 40155 | (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carbonyl chloride | C24H31ClO4 | 详情 | 详情 | |
| (VI) | 40154 | (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-5-(4-morpholinylcarbonyl)-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-14,16-dione | C28H39NO5 | 详情 | 详情 |