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【结 构 式】

【分子编号】32828

【品名】(2S)-4-(4-methoxyphenyl)-2-[(2,2,2-trifluoroacetyl)amino]butyric acid

【CA登记号】

【 分 子 式 】C13H14F3NO4

【 分 子 量 】305.2537096

【元素组成】C 51.15% H 4.62% F 18.67% N 4.59% O 20.97%

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:(XVIII)

The chiral intermediate 7-methoxy-1,2,3,4-tetrahydronaphthalen-2(S)-amine (IV) has also been obtained as follows: The Friedel Crafts condensation of anisole (XV) with N-trifluoroacetyl-L-aspartic acid anhydride (XVI) by means of AlCl3 in dichloromethane gives 4-(4-methoxyphenyl)-4-oxo-2(S)-(trifluoro-acetamido)butyric acid (XVII), which is hydrogenated with H2 over Pd/C in ethanol/H2SO4 yielding 4-(4-methoxyphenyl)-2(S)-(trifluoroacetamido)butyric acid (XVIII). The cyclization of (XVIII) by its reaction with PCl5, followed by a treatment with SnCl4 provides the tetralone (XIX), which is hydrogenated as before to give N-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2(S)-yl)trifluoro-acetamide (XX). Finally, this compound is deacetylated with HCl in ethanol to provide the chiral intermediate the amine (IV).

1 Devocelle, M.; et al.; Alternative synthesis of the chiral atypical beta-adrenergic phenylethanolaminotetraline agonist SR58611A using enantioselective hydrogenation. Tetrahedron Lett 1999, 40, 24, 4551.
2 Cecchi, R.; et al.; Synthesis and beta-adrenergic activity of atypical beta-adrenergic phenylethanolaminotetralin stereoisomers. Eur J Med Chem 1994, 29, 4, 259.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 32820 (2S)-7-methoxy-1,2,3,4-tetrahydro-2-naphthalenylamine; (2S)-7-methoxy-1,2,3,4-tetrahydro-2-naphthalenamine C11H15NO 详情 详情
(XV) 18410 N-[(3S)-2,5-dioxotetrahydro-3-furanyl]-2,2,2-trifluoroacetamide 777-33-3 C6H4F3NO4 详情 详情
(XVI) 23767 Methoxybenzene; Methyl phenyl ether; Anisole 100-66-3 C7H8O 详情 详情
(XVII) 32827 (2S)-4-(4-methoxyphenyl)-4-oxo-2-[(2,2,2-trifluoroacetyl)amino]butyric acid C13H12F3NO5 详情 详情
(XVIII) 32828 (2S)-4-(4-methoxyphenyl)-2-[(2,2,2-trifluoroacetyl)amino]butyric acid C13H14F3NO4 详情 详情
(XIX) 32829 2,2,2-trifluoro-N-[(2S)-7-methoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl]acetamide C13H12F3NO3 详情 详情
(XX) 32830 2,2,2-trifluoro-N-[(2S)-7-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]acetamide C13H14F3NO2 详情 详情
Extended Information