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【结 构 式】

【分子编号】51636

【品名】4-Chloro-2-methoxy-1-nitrobenzene; 4-Chloro-2-methoxynitrobenzene; 5-Chloro-2-nitroanisole

【CA登记号】6627-53-8

【 分 子 式 】C7H6ClNO3

【 分 子 量 】187.58228

【元素组成】C 44.82% H 3.22% Cl 18.9% N 7.47% O 25.59%

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 condensation of 5-chloro-2-nitroanisole (V) with diethyl malonate (VI) by means of NaH in hot DMF gives 2-(3-methoxy-4-nitrophenyl)malonic acid diethyl ester (VII), which is reduced with H2 over Pd/C in ethyl acetate, yielding the corresponding amino derivative (VIII). The condensation of (VIII) with 2-methylphenyl isocyanate (IX) by means of TEA in dichloromethane affords the expected urea (X), which is submitted to a decarboxylative hydrolysis with NaOH in refluxing tert-butanol to provide the phenylacetic acid (XI). The condensation of acetic acid (XI) with the amino group of the isoxazole intermediate (IV) by means of HOBt, DIEA and EDC in DMF gives the amide (XII), which is treated with NaOH in tert-butanol to afford the target propionic acid.

1 Duplantier, A.J.; et al.; Isoxazolyl, oxazolyl, and thiazolylpropionic acid derivatives as potent alpha4beta1 integrin antagonists. Bioorg Med Chem Lett 2001, 11, 19, 2593.
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) 51635 methyl 3-[3-[(1S)-1-amino-3-methylbutyl]-5-isoxazolyl]propanoate C12H20N2O3 详情 详情
(V) 51636 4-Chloro-2-methoxy-1-nitrobenzene; 4-Chloro-2-methoxynitrobenzene; 5-Chloro-2-nitroanisole 6627-53-8 C7H6ClNO3 详情 详情
(VI) 16829 Diethyl malonate 105-53-3 C7H12O4 详情 详情
(VII) 51637 diethyl 2-(3-methoxy-4-nitrophenyl)malonate C14H17NO7 详情 详情
(VIII) 51638 diethyl 2-(4-amino-3-methoxyphenyl)malonate C14H19NO5 详情 详情
(IX) 27106 1-isocyanato-2-methylbenzene 614-68-6 C8H7NO 详情 详情
(X) 51639 diethyl 2-[3-methoxy-4-[(2-toluidinocarbonyl)amino]phenyl]malonate C22H26N2O6 详情 详情
(XI) 39718 2-[3-methoxy-4-[(2-toluidinocarbonyl)amino]phenyl]acetic acid C17H18N2O4 详情 详情
(XII) 51640 methyl 3-(3-[(1S)-1-[(2-[3-methoxy-4-[(2-toluidinocarbonyl)amino]phenyl]acetyl)amino]-3-methylbutyl]-5-isoxazolyl)propanoate C29H36N4O6 详情 详情
Extended Information