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【结 构 式】 
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【分子编号】68025 【品名】1-(3-amino-5-(benzyloxy)-2-hydroxyphenyl)ethanone 【CA登记号】 |
【 分 子 式 】C15H15NO3 【 分 子 量 】257.28904 【元素组成】C 70.02% H 5.88% N 5.44% O 18.66% |
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：(XIV)Selective O-protection of 2,5-dihydroxyacetophenone (XI) with benzyl bromide by means of K2Co3 in acetone or methylisobutylketone yields 2’-hydroxy-5’-benzyloxyacetophenone (XII) , which is then nitrated with fuming Hno3 in AcoH to give the 3’-nitroacetophenone derivative (XIII) . Reduction of the nitro group in compound (XIII) by catalytic hydrogenation over Rh/C in MeoH or Pto2 in 2-MeTHF (4, 5) provides the corresponding aniline (XIV) , which finally undergoes cyclization with chloroacetyl chloride (XV) in the presence of K2Co3 in refluxing acetonitrile or 2-MeTHF .
| 【1】 Bouyssou, T., Hoenke, C., Rudolf, K. et al. Discovery of olodaterol, a novel inhaled b2-adrenoceptor agonist with a 24 h bronchodilatory efficacy. Bioorg Med Chem Lett 2010, 20(4): 1410-4. |
| 【2】 Konetzki, I., Lustenberger, P., Sieger, P. (Boehringer Ingelheim Pharma GmbH & Co. KG). Novel enantiomerically pure beta-agonists, method for the production and the use thereof in the form of a drug. EP 1789405, JP 2007537196, US 2005267106, US 2007027148, US 7220742, US 7491719, US 2009137578, US 8034809, Wo 2005111005. |
| 【3】 Krueger, T., Ries, U., Schnaubelt, J., Rall, W., Leuter, Z.A., Duran, A., Soyka, R. (Boehringer Ingelheim Pharma GmbH & Co. KG). Method for producing betamimetics. EP 1917253, JP 2009504708, US 201114859, Wo 2007020227. |
| 【4】 Rodriguez Dehli, J.M., Hagenkoetter, R., Schul, M., Stange, C. (Boehringer Ingelheim Pharma GmbH & Co. KG). Method for producing betamimetics. EP 2125759, JP 2010516739, US 2010022770, Wo 2008090193. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 68012 | 8-acetyl-6-benzyloxy-1,4-benzoxazin-3-one | C17H15NO4 | 详情 | 详情 | |
| (XI) | 38479 | 1-(2,5-dihydroxyphenyl)-1-ethanone | 490-78-8 | C8H8O3 | 详情 | 详情 |
| (XII) | 20133 | 1-[5-(benzyloxy)-2-hydroxyphenyl]-1-ethanone | C15H14O3 | 详情 | 详情 | |
| (XIII) | 68024 | 1-(5-(benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone | C15H13NO5 | 详情 | 详情 | |
| (XIV) | 68025 | 1-(3-amino-5-(benzyloxy)-2-hydroxyphenyl)ethanone | C15H15NO3 | 详情 | 详情 | |
| (XV) | 11296 | 2-Chloroacetyl chloride; Chloroacetic chloride | 79-04-9 | C2H2Cl2O | 详情 | 详情 |
Extended Information