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【结 构 式】

【分子编号】68024

【品名】1-(5-(benzyloxy)-2-hydroxy-3-nitrophenyl)ethanone

【CA登记号】 

【 分 子 式 】C15H13NO5

【 分 子 量 】287.27196

【元素组成】C 62.72% H 4.56% N 4.88% O 27.85%

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:(XIII)

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