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【结 构 式】 
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【药物名称】Ono-3144 【化学名称】1-[3-(Aminomethyl)-5-(1,1-dimethylethyl)-2-hydroxyphenyl]-1-propanone hydrochloride 【CA登记号】75060-92-3 (free base) 【 分 子 式 】C14H22ClNO2 【 分 子 量 】271.78994 |
【开发单位】Ono (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Non-Opioid Analgesics, Non-Steroidal Antiinflammatory Drugs |
合成路线1
The Friedel-Kraft's condensation of 4-tert-butylphenol (I) with propionyl chloride (II) by means of FeCl3 in methylene chloride gives 2-hydroxy-5-tert-butylpropiophenone (III), which is then condensed with chloroacetylaminomethanol (IV) by means of H2SO4 in acetic acid affording 3-(chloroacetylaminomethyl)-5-tert-butyl-2-hydroxypropiophenone (V). Finally, this compound is hydrolyzed with HCl in methanol.
| 【1】 Hashimoto, K.; ONO-3144. Drugs Fut 1985, 10, 10, 825. |
| 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) | 29734 | 4-(tert-butyl)phenol | 98-54-4 | C10H14O | 详情 | 详情 |
| (II) | 15967 | propanoyl chloride; propionyl chloride | 79-03-8 | C3H5ClO | 详情 | 详情 |
| (III) | 29735 | 1-[5-(tert-butyl)-2-hydroxyphenyl]-1-propanone | C13H18O2 | 详情 | 详情 | |
| (IV) | 23020 | 2-chloro-N-(hydroxymethyl)acetamide | 2832-19-1 | C3H6ClNO2 | 详情 | 详情 |
| (V) | 29736 | N-[5-(tert-butyl)-2-hydroxy-3-propionylbenzyl]-2-chloroacetamide | C16H22ClNO3 | 详情 | 详情 |