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【结 构 式】 
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【分子编号】24074 【品名】2-[(3,4-dihydro-2H-thiochromen-8-yloxy)methyl]oxirane 【CA登记号】 |
【 分 子 式 】C12H14O2S 【 分 子 量 】222.30796 【元素组成】C 64.83% H 6.35% O 14.39% S 14.42% |
合成路线1
该中间体在本合成路线中的序号：(V)The cyclization of 3-(2-methoxyphenylthio)propionic acid (II) with PPA yields 8 methoxythiochroman-4-one (III). Thiochromanone (III) is then reduced to 8-hydroxythiochromane (IV) by the Wolff-Kishner reduction method. Demethylation is almost complete during this reduction. The 8-hydroxythiochromane (IV), treated with epichlorohydrin, yields the corresponding epoxide (V), which when treated with excess tert-butylamine yields tertatolol base.
| 【1】 Leclerc, G.; Tertatolol hydrochloride. Drugs Fut 1986, 11, 2, 131. |
| 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) | 24070 | 2-methoxyphenylhydrosulfide | 7217-59-6 | C7H8OS | 详情 | 详情 |
| (II) | 24071 | 3-[(2-methoxyphenyl)sulfanyl]propionic acid | C10H12O3S | 详情 | 详情 | |
| (III) | 24072 | 8-methoxy-2,3-dihydro-4H-thiochromen-4-one | C10H10O2S | 详情 | 详情 | |
| (IV) | 24073 | 8-thiochromanol | C9H10OS | 详情 | 详情 | |
| (V) | 24074 | 2-[(3,4-dihydro-2H-thiochromen-8-yloxy)methyl]oxirane | C12H14O2S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)2) The reaction of indomethacin (III) with thionyl chloride in hot toluene gives the corresponding acyl chloride (IV), which is then condensed with tropic acid (V) in refluxing toluene containing pyridine to afford title compound.
| 【1】 Nemecek, O.; Fisnerova, L.; Grimova, J.; Roubal, Z. (SPOFA - United Pharmaceutical Works); 2-Phenyl-2-carboxyethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate and process for preparation thereof. US 4136194 . |
| 【2】 Fisnerova, L.; Tropesin. Drugs Fut 1986, 11, 9, 779. |
| 【3】 Fisnerova, L.; et al.; Pharmacologically interesting indomethacin derivatives. Cesk Farm 1977, 26, 6, 227-31. |