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【结 构 式】 
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【分子编号】34105 【品名】ethyl (Z)-2-[formyl[(1R)-1-phenylethyl]amino]-3-hydroxy-2-propenoate 【CA登记号】 |
【 分 子 式 】C14H17NO4 【 分 子 量 】263.29332 【元素组成】C 63.87% H 6.51% N 5.32% O 24.31% |
合成路线1
该中间体在本合成路线中的序号：(V)The reaction of dl-l-phenylethylamine (I) with ethyl chloroacetate (II) by means of triethylamine in DMF gives dl-N-[(ethoxycarbonyl)methyl]-1-phenylethylamine (III), which is then treated with formic acid in refluxing xylene yielding dl-N-formyl-N-[(ethoxycarbonyl)methyl]-1-phenylethylamine (IV). The reaction of (IV) with sodium ethoxide and ethyl formate (A) in THF affords dl-N-formyl-N-[(ethoxycarbonyl)-2-hydroxyvinyl]-1-phenylethylamine (V), which, without purification, is treated with potassium thiocyanate and HCl in diisopropyl ether to give dl-l-(phenylethyl)-2-mercapto-5-ethoxycarbonylimidazole (VI). This product is finally treated with nitric acid and sodium nitrate at room temperature. The optical active drugs can be obtained starting the synthesis with the optically active amine (I).
| 【1】 Godefroi, E.F.; et al.; Imidazole carboxylates. BE 0662474; DE 1545988; FR 4499M; GB 1064531; US 3354173 . |
| 【2】 Roberts, P.J.; Castaner, J.; Etomidate. Drugs Fut 1976, 1, 10, 461. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 16602 | ethyl formate | 109-94-4 | C3H6O2 | 详情 | 详情 |
| (I) | 10039 | (1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine | 3886-69-9 | C8H11N | 详情 | 详情 |
| (II) | 16601 | ethyl chloroacetate; ethyl 2-chloroacetate | 105-39-5 | C4H7ClO2 | 详情 | 详情 |
| (III) | 34103 | ethyl 2-[[(1R)-1-phenylethyl]amino]acetate | C12H17NO2 | 详情 | 详情 | |
| (IV) | 34104 | ethyl 2-[formyl[(1R)-1-phenylethyl]amino]acetate | C13H17NO3 | 详情 | 详情 | |
| (V) | 34105 | ethyl (Z)-2-[formyl[(1R)-1-phenylethyl]amino]-3-hydroxy-2-propenoate | C14H17NO4 | 详情 | 详情 | |
| (VI) | 34106 | ethyl 1-[(1R)-1-phenylethyl]-2-sulfanyl-1H-imidazole-5-carboxylate | C14H16N2O2S | 详情 | 详情 |