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【结 构 式】

【分子编号】61873

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

【CA登记号】

【 分 子 式 】C31H31F3N2O5

【 分 子 量 】568.5928296

【元素组成】C 65.48% H 5.5% F 10.02% N 4.93% O 14.07%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

The title enantiomer has been obtained by resolution of the racemic acid (I). Acid (I) is activated as the mixed anhydride (II) with pivalic acid and triethylamine. Subsequent coupling of anhydride (II) with the potassium anion of (S)-4-benzyl-2-oxazolidinone leads to a mixture of the diastereoisomeric imides (III) and (IV), which can be separated by column chromatography and recrystallization. Then, removal of the chiral auxiliary from the target isomer (III) by hydrolysis with lithium peroxide furnishes the desired (S)-enantiomer.

1 Miyachi, H.; Nomura, M.; Tanase, T.; Suzuki, M.; Murakami, K.; Awano, K.; Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha. Bioorg Med Chem Lett 2002, 12, 3, 333.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
14694 (S)-4-Benzyl-2-oxazolidinone; (4S)-4-Benzyl-1,3-oxazolan-2-one; (S)-(-)-4-Benzyl-2-oxazolidinone 90719-32-7 C10H11NO2 详情 详情
(I) 61870 2-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)benzyl]butanoic acid C21H22F3NO4 详情 详情
(II) 61871 1,1-dimethylpropanoic 1-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)benzyl]butanoic anhydride C26H30F3NO5 详情 详情
(III) 61872 5-((2S)-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
(IV) 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

合成路线2

该中间体在本合成路线中的序号:(VII)

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