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【结 构 式】

【分子编号】61876

【品名】5-((2S)-2-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}butyl)-2-methoxybenzoic acid

【CA登记号】

【 分 子 式 】C23H25NO6

【 分 子 量 】411.45464

【元素组成】C 67.14% H 6.12% N 3.4% O 23.33%

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:(IV)

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
Extended Information