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【结 构 式】

【分子编号】37196

【品名】1-[4-(tert-butyl)phenyl]-N-[(2S)-2-(4-methylphenyl)propyl]-5-oxo-3-pyrrolidinecarboxamide

【CA登记号】

【 分 子 式 】C25H32N2O2

【 分 子 量 】392.54136

【元素组成】C 76.5% H 8.22% N 7.14% O 8.15%

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:(V)

The Michael addition of 4-tert-butylaniline (I) with 2-methylenesuccinic acid (II) followed by cyclization gives racemic 1-(4-tert-butylphenyl)-5-oxopyrrolidine-3-carboxylic acid (III) (1), which is treated with SOCl2 and condensed with (S)(-)-1-(4-methylphenyl)ethylamine (IV) to yield a diastereomeric mixture of amides (V). The resolution of (V) by silicagel chromatography affords the (S,S)-diastereomer (VI), which is treated with N2O4 and NaOAc in CCl4 to provide 1-(4-tert-butylphenyl)-5-oxopyrrolidine-3(S)-carboxylic acid (VII). The reduction of (VII) with BH3/THF in dichloromethane gives the corresponding carbinol (VIII), which is treated with MsCl and TEA in dichloromethane to yield the mesylate (IX). The condensation of (IX) with 4-hydroxybenzoic acid methyl ester (X) by means of K2CO3 in DMF affords the corresponding phenyl ether (XI), which is finally hydrolyzed with HCl/AcOH to furnish the target compound.

1 Ohno, T.; Ogawa, K.; Yano, S.; Kobayashi, K.; Shirasaka, T.; Yamada, H.; Yamamoto, A.; Synthesis of the optical isomers of 4-[1-(4-tert-butylphenyl)-2-oxo-pyrrolidine-4-yl]methyloxybenzoic acid (S-2) and their biological evaluation as antilipidemic agent. Chem Pharm Bull 1999, 47, 11, 1549.
2 Watanabe, S.; et al.; Synthesis of 4-[1-(substituted phenyl)-2-oxo-pyrrolidin-4-yl]methyloxybenzoic acids and related compounds, and their inhibitory capacities toward fatty-acid and sterol biosyntheses. Eur J Med Chem 1994, 29, 675.
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) 27492 4-(tert-butyl)aniline 769-92-6 C10H15N 详情 详情
(II) 27493 2-methylenesuccinic acid 97-65-4 C5H6O4 详情 详情
(III) 27494 1-[4-(tert-butyl)phenyl]-5-oxo-3-pyrrolidinecarboxylic acid C15H19NO3 详情 详情
(IV) 37195 (2S)-2-(4-methylphenyl)-1-propanamine; (2S)-2-(4-methylphenyl)propylamine C10H15N 详情 详情
(V) 37196 1-[4-(tert-butyl)phenyl]-N-[(2S)-2-(4-methylphenyl)propyl]-5-oxo-3-pyrrolidinecarboxamide C25H32N2O2 详情 详情
(VI) 37197 (3S)-1-[4-(tert-butyl)phenyl]-N-[(2S)-2-(4-methylphenyl)propyl]-5-oxo-3-pyrrolidinecarboxamide C25H32N2O2 详情 详情
(VII) 37198 (3S)-1-[4-(tert-butyl)phenyl]-5-oxo-3-pyrrolidinecarboxylic acid C15H19NO3 详情 详情
(VIII) 27499 (4S)-1-[4-(tert-butyl)phenyl]-4-(hydroxymethyl)-2-pyrrolidinone C15H21NO2 详情 详情
(IX) 37199 (4S)-1-[4-(tert-butyl)phenyl]-4-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-2-pyrrolidinone C18H27NO2S 详情 详情
(X) 10251 methyl 4-hydroxybenzoate; Methyl p-hydroxybenzoate 99-76-3 C8H8O3 详情 详情
(XI) 27501 methyl 4-([(3S)-1-[4-(tert-butyl)phenyl]-5-oxopyrrolidinyl]methoxy)benzoate C23H27NO4 详情 详情
Extended Information