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【结 构 式】 
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【分子编号】30637 【品名】ethyl 7-[(1R)-2-[(benzyloxy)carbonyl]-1-methyl-2,3-dihydro-1H-isoindol-5-yl]-1-cyclopropyl-8-(difluoromethoxy)-4-oxo-1,4-dihydro-3-quinolinecarboxylate 【CA登记号】 |
【 分 子 式 】C33H30F2N2O6 【 分 子 量 】588.6078864 【元素组成】C 67.34% H 5.14% F 6.46% N 4.76% O 16.31% |
合成路线1
该中间体在本合成路线中的序号：(XXII)The reaction of 2-(benzyloxycarbonyl)-5-bromo-1(R)-methylisoindoline (XX) with hexabutyldistannane and bis(triphenylphosphine)palladium(II) chloride in toluene gives the corresponding tributyltin derivative (XXI), which is condensed with the previously described quinolone (XVI) by means of the palladium catalyst as before, yielding the protected compound (XXII), which is deprotected by hydrolysis of the ester group with NaOH, followed by hydrogenolysis with H2 over Pd/C in acetic acid.
| 【1】 Yamada, M.; Takahata, M.; Ojima, K.; Todo, Y.; Kito, T.; Hayashi, H.; Watanabe, Y.; Narita, H.; Hamamoto, S.; T-3811, a novel des-F(6)-quinolone: Synthesis and in vitro activity of 7-(isoindolin-5-yl) derivatives. 37th Intersci Conf Antimicrob Agents Chemother (Sept 28-Oct 1, Toronto) 1997, Abst F-158. |
| 【2】 Castañer, J.; Rabasseda, X.; Graul, A.; T-3811ME. Drugs Fut 1999, 24, 12, 1324. |
| 【3】 Todo, Y.; Hayashi, K.; Takahata, M.; Watanabe, Y.; Narita, H. (Toyama Chemical Co., Ltd.); Quinolonecarboxylic acid derivs. or salts thereof.. EP 0882725; US 6025370; WO 9729102 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVI) | 30631 | ethyl 7-bromo-1-cyclopropyl-8-(difluoromethoxy)-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C16H14BrF2NO4 | 详情 | 详情 | |
| (XX) | 30635 | benzyl (1R)-5-bromo-1-methyl-1,3-dihydro-2H-isoindole-2-carboxylate | C17H16BrNO2 | 详情 | 详情 | |
| (XXI) | 30636 | benzyl (1R)-1-methyl-5-(tributylstannyl)-1,3-dihydro-2H-isoindole-2-carboxylate | C29H43NO2Sn | 详情 | 详情 | |
| (XXII) | 30637 | ethyl 7-[(1R)-2-[(benzyloxy)carbonyl]-1-methyl-2,3-dihydro-1H-isoindol-5-yl]-1-cyclopropyl-8-(difluoromethoxy)-4-oxo-1,4-dihydro-3-quinolinecarboxylate | C33H30F2N2O6 | 详情 | 详情 |