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【结 构 式】 
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【分子编号】36097 【品名】2-[2-(2,3-dihydroxypropoxy)phenoxy]-N-methylacetamide 【CA登记号】 |
【 分 子 式 】C12H17NO5 【 分 子 量 】255.27072 【元素组成】C 56.46% H 6.71% N 5.49% O 31.34% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of 2-(N-methylcarbamoylmethoxy)phenol (I) with 3-benzyloxy-1-(p-toluenesulfonyloxy)-2-propanol (II) by means of Na in refluxing methoxyethanol gives 3 benzyloxy-1-[2-(N-methylcarbamoylmethoxy)phenoxy]-2-propanol (III), which is debenzylated by hydrogenolysis with H2 over Pd/C in methanol yielding 1-[2-(N-methylcarbamoylmethoxy)phenoxy]-2,3-propanediol (IV). The tosylation of (IV) with tosyl chloride in pyridine affords 1-[2-(N-methylcarbamoylmethoxy)phenoxy]-3-tosyloxy-2-propanol (V), which by treatment with NaOH in water is converted into 1-[2-(N-methylcarbamoylmethoxy)phenoxy]-2,3-epoxypropane (VI). Finally, this compound is treated with tertbutylamine in refluxing tert-butanol.
| 【1】 Tucker, H.; FR 2250752 . |
| 【2】 Hillier, K.; Castaner, J.; Blancafort, P.; Serradell, M.N.; Cetamolol hydrochloride. Drugs Fut 1983, 8, 4, 305. |
| 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) | 36094 | 2-(2-hydroxyphenoxy)-N-methylacetamide | C9H11NO3 | 详情 | 详情 | |
| (II) | 36095 | 3-(benzyloxy)-2-hydroxypropyl 4-methylbenzenesulfonate | C17H20O5S | 详情 | 详情 | |
| (III) | 36096 | 2-[2-[3-(benzyloxy)-2-hydroxypropoxy]phenoxy]-N-methylacetamide | C19H23NO5 | 详情 | 详情 | |
| (IV) | 36097 | 2-[2-(2,3-dihydroxypropoxy)phenoxy]-N-methylacetamide | C12H17NO5 | 详情 | 详情 | |
| (V) | 36098 | 2-hydroxy-3-[2-[2-(methylamino)-2-oxoethoxy]phenoxy]propyl 4-methylbenzenesulfonate | C19H23NO7S | 详情 | 详情 | |
| (VI) | 36099 | N-methyl-2-[2-(2-oxiranylmethoxy)phenoxy]acetamide | C12H15NO4 | 详情 | 详情 | |
| (VII) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |