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【结 构 式】 
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【分子编号】40412 【品名】N-(4-methoxyphenyl)-2,2-dimethylpropanamide 【CA登记号】 |
【 分 子 式 】C12H17NO2 【 分 子 量 】207.27252 【元素组成】C 69.54% H 8.27% N 6.76% O 15.44% |
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 acylation of 4-methoxyaniline (I) with pivaloyl chloride (II) and TEA in CH2Cl2 gives the anilide (III), which is condensed with ethyl trifluoroacetate (IV) by means of n-BuLi in THF yielding the trifluoroacetyl derivative (V). The hydrolysis of the amido group of (V) with 6N HCl in refluxing DMF affords the 2-aminoacetophenone (VI), which is condensed with cyclopropylacetylene (VII) by means of n-BuLi in THF to give the tertiary alcohol (VIII). Finally, this compound is cyclized with phosgene and DIPEA in toluene yielding the racemic form of target compound.
| 【1】 Ko, S.S.; Patel, M.; Cordova, B.C.; Klabe, R.M.; Srivastava, A.S.; Markwalder, J.A.; McHugh, R.J. Jr.; Seitz, S.P.; Trainor, G.L.; Erickson-Vittanen, S.; Synthesis and evaluation of analogs of efavirenz (Sustiva(TM)) as HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem Lett 1999, 9, 19, 2805. |
| 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) | 10478 | p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine | 104-94-9 | C7H9NO | 详情 | 详情 |
| (II) | 13597 | 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride | 3282-30-2 | C5H9ClO | 详情 | 详情 |
| (III) | 40412 | N-(4-methoxyphenyl)-2,2-dimethylpropanamide | C12H17NO2 | 详情 | 详情 | |
| (IV) | 14588 | Ethyl 2,2,2-trifluoroacetate; Trifluoroethyl acetate | 383-63-1 | C4H5F3O2 | 详情 | 详情 |
| (V) | 40413 | N-[4-methoxy-2-(2,2,2-trifluoroacetyl)phenyl]-2,2-dimethylpropanamide | C14H16F3NO3 | 详情 | 详情 | |
| (VI) | 40414 | 1-(2-amino-5-methoxyphenyl)-2,2,2-trifluoro-1-ethanone | C9H8F3NO2 | 详情 | 详情 | |
| (VII) | 16575 | 1-ethynylcyclopropane; cyclopropyl acetylene | 6746-94-7 | C5H6 | 详情 | 详情 |
| (VIII) | 40415 | 2-(2-amino-5-methoxyphenyl)-4-cyclopropyl-1,1,1-trifluoro-3-butyn-2-ol | C14H14F3NO2 | 详情 | 详情 |
Extended Information