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【结 构 式】 
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【分子编号】61875 【品名】benzyl 5-((2S)-2-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}butyl)-2-methoxybenzoate 【CA登记号】 |
【 分 子 式 】C30H31NO6 【 分 子 量 】501.57928 【元素组成】C 71.84% H 6.23% N 2.79% O 19.14% |
合成路线1
该中间体在本合成路线中的序号：(III)In an enantioselective synthesis of the (S)-enantiomer, asymmetric alkylation of the chiral N-butyryl oxazolidinone (I) with benzyl 5-bromomethyl-2-methoxybenzoate (II) in the presence of lithium hexamethyldisilazide leads to isomer (III) in high diastereomeric excess. Subsequent benzyl ester hydrogenolysis in (III) employing Pd/C affords carboxylic acid (IV), which is further converted to the mixed anhydride (V) with ethyl chloroformate and triethylamine. Coupling of anhydride (V) with 4-trifluoromethylbenzylamine (VI) furnishes the corresponding amide (VII). The chiral auxiliary is then removed from (VII) by hydrolysis with lithium peroxide to yield the target (S)-enantiomer.
| 【1】 Nomura, M.; Tanase, T.; Miyachi, H.; Efficient asymmetric synthesis of (S)-2-ethylphenylpropanoic acid derivative, a selective agonist for human peroxisome proliferator-activated receptor alpha. Bioorg Med Chem Lett 2002, 12, 16, 2101. |
| 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) | 10794 | (4S)-4-Benzyl-3-butyryl-1,3-oxazolan-2-one | C14H17NO3 | 详情 | 详情 | |
| (II) | 61874 | benzyl 5-(bromomethyl)-2-methoxybenzoate | C16H15BrO3 | 详情 | 详情 | |
| (III) | 61875 | benzyl 5-((2S)-2-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}butyl)-2-methoxybenzoate | C30H31NO6 | 详情 | 详情 | |
| (IV) | 61876 | 5-((2S)-2-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}butyl)-2-methoxybenzoic acid | C23H25NO6 | 详情 | 详情 | |
| (V) | 61877 | C26H29NO8 | 详情 | 详情 | ||
| (VI) | 21925 | [4-(trifluoromethyl)phenyl]methanamine; 4-(trifluoromethyl)benzylamine | 3300-51-4 | C8H8F3N | 详情 | 详情 |
| (VII) | 61873 | 5-((2R)-2-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}butyl)-2-methoxy-N-[4-(trifluoromethyl)benzyl]benzamide | C31H31F3N2O5 | 详情 | 详情 |