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【结 构 式】 
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【分子编号】30754 【品名】methyl 5-acetyl-2-[(2-oxotetrahydro-3-furanyl)oxy]benzoate 【CA登记号】 |
【 分 子 式 】C14H14O6 【 分 子 量 】278.26156 【元素组成】C 60.43% H 5.07% O 34.5% |
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：(III)The reaction of methyl-5-acetylsalicylate (I) with alpha-bromo-gamma-butyrolactone (II) by means of K2CO3 in refluxing acetone gives alpha-[(2-methoxycarbonyl-4-acetylphenyl)oxy]-gamma-butyrolactone (III), which is hydrolyzed with NaOH in methanol yielding alpha-[(2-carboxy-4-acetylphenyl)oxy]-gamma-butyrolactone (IV). The cyclization of (IV) with refluxing acetic anhydride affords 5-acetyl-4',5'-dihydrospiro[benzofuran-2(3H),3'(2'H)-furan]-2',3-dione (V), which is finally treated at 155 C in dimethylsulfoxide containing NaCl.
| 【1】 Hirosada, S.; Watanabe, M.; Mitsuru, K.; Isuke, I. (Takeda Chemical Industries, Ltd.); Spirobenzofuranone compounds, processes for their preparation and their use as medicines. CA 1113467; DE 2861651; EP 0003084; ES 476330; ES 8102114; JP 54098752; ZA 7807296 . |
| 【2】 Blancafort, P.; Castaner, J.; Serradell, M.N.; AG-629. Drugs Fut 1983, 8, 2, 92. |
| 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) | 30753 | methyl 5-acetyl-2-hydroxybenzoate | 16475-90-4 | C10H10O4 | 详情 | 详情 |
| (II) | 22822 | 3-bromodihydro-2(3H)-furanone | 5061-21-2 | C4H5BrO2 | 详情 | 详情 |
| (III) | 30754 | methyl 5-acetyl-2-[(2-oxotetrahydro-3-furanyl)oxy]benzoate | C14H14O6 | 详情 | 详情 | |
| (IV) | 30755 | 5-acetyl-2-[(2-oxotetrahydro-3-furanyl)oxy]benzoic acid | C13H12O6 | 详情 | 详情 | |
| (V) | 30756 | 5-Acetyl-2,2',3,3',4',5'-hexahydrospiro[benzofuran-2,2'-furan]-3,3'-dione | C13H10O5 | 详情 | 详情 |
Extended Information