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【结 构 式】 
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【分子编号】26458 【品名】N-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-N-methyl-2-(4-nitrophenoxy)-1-ethanamine 【CA登记号】 |
【 分 子 式 】C30H36N2O5 【 分 子 量 】504.62632 【元素组成】C 71.41% H 7.19% N 5.55% O 15.85% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of 5-(benzyloxy)-2,2,4,6,7-pentamethyl-3,4-dihydrobenzofuran-3-ylmethyl methanesulfonate (I) with 2-(methylamino)ethanol (II) by heating at 120 C gives the tertiary amine (III), which is treated with SOCl2 in benzene yielding the chloroethylamino compound (IV). The condensation of (IV) with 4-nitrophenol (V) by means of K2CO3 in hot DMF affords the 4-nitrophenoxy compound (VI), which is reduced with H2 over Pd/C in ethyl acetate to the corresponding 4-aminophenoxy compound (VII). The condensation of (VII) with ethyl acrylate (VIII) by means of NaNO2 and HBr in methanol/water gives the 2-bromopropionic ester (IX), which is cyclized with thiourea (X) by means of NaOAc in refluxing ethanol yielding the thiazolidinedione (XI). Finally, this compound is debenzylated with HCl in hot acetic acid.
| 【1】 Casturi, S.R.; Lohray, V.B.; Kallam, A.R.; Pingali, H.; Ramanujam, R.; Alla, S.R. (Dr. Reddy's Research Foundation); Cpds. having antidiabetic, hypolipidemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5925656 . |
| 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) | 26455 | 5-(benzyloxy)-2,2,4,6,7-pentamethyl-3-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-2,3-dihydro-1-benzofuran | C24H32O3S | 详情 | 详情 | |
| (II) | 13324 | 2-Methylaminoethanol; 2-(Methylamino)-1-ethanol | 109-83-1 | C3H9NO | 详情 | 详情 |
| (III) | 26456 | 2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]-1-ethanol | C24H33NO3 | 详情 | 详情 | |
| (IV) | 26457 | N-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-2-chloro-N-methyl-1-ethanamine | C24H32ClNO2 | 详情 | 详情 | |
| (V) | 11236 | 4-Nitrophenol; p-Nitrophenol | 100-02-7 | C6H5NO3 | 详情 | 详情 |
| (VI) | 26458 | N-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-N-methyl-2-(4-nitrophenoxy)-1-ethanamine | C30H36N2O5 | 详情 | 详情 | |
| (VII) | 26459 | 4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]aniline | C30H38N2O3 | 详情 | 详情 | |
| (VIII) | 10164 | ethyl acrylate | 140-88-5 | C5H8O2 | 详情 | 详情 |
| (IX) | 26460 | ethyl 3-(4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]phenyl)-2-bromopropanoate | C35H44BrNO5 | 详情 | 详情 | |
| (X) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (XI) | 26461 | 5-(4-[2-[[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl](methyl)amino]ethoxy]benzyl)-1,3-thiazolidine-2,4-dione | C34H40N2O5S | 详情 | 详情 |