• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】Etomidate, R-16659, Hypnomidate, Amidate

【化学名称】(+)-1-[1(R)-Phenylethyl]-1H-imidazole-5-carboxylic acid ethyl ester

【CA登记号】33125-97-2

【 分 子 式 】C14H16N2O2

【 分 子 量 】244.29582

【开发单位】Janssen (Originator)

【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Anesthetic Drugs, General Anesthetics, Intravenous Anesthetics

合成路线1

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
Extended Information