• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】62684

【品名】3-(4-iodophenyl)-3-methyl-2-oxiranecarboxylic acid

【CA登记号】

【 分 子 式 】C10H9IO3

【 分 子 量 】304.08413

【元素组成】C 39.5% H 2.98% I 41.73% O 15.78%

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)

The Darzen's condensation of 4-iodoacetophenone (I) with methyl chloroacetate (II) in the presence of NaOMe afforded the glycidic ester (III), which was further hydrolyzed to the corresponding glycidic acid (IV) with NaOH in aqueous ethanol. Subsequent decarboxylation of (IV) under acidic conditions furnished 2-(4-iodophenyl)propionaldehyde (V). After oxidation of aldehyde (V) with sodium chlorite, the resultant carboxylic acid was converted to the corresponding zinc salt (VI) upon treatment with ZnCl2 and NaOH. Coupling of aryl iodide (VI) with the Grignard reagent (VIII) (prepared from 2-bromo-3-methylthiophene (VII)) in the presence of PdCl2 gave rise to the racemic biarylpropionic acid (IX)). The title (R)-enantiomer was then resolved via formation of the diastereoisomeric salts with D-phenylglycine methyl ester (X)

2 Arai, H.; Tanaka, K.; Watanabe, I.; Kodama, T.; Hirano, H.; Abe, N.; Nakabayashi, M. (Toyama Chemical Co., Ltd.); Novel 2-[4-(3-methyl-2-thienyl)phenyl]propionic acid and pharmaceutically acceptable salt thereof and method for treating symptoms of inflammation and pain. US 4230719 .
1 Kodama, T.; Nakabayashi, M.; Watanabe, I.; Hirano, Y.; Abe, N.; Tanaka, K.; Arai, H. (Toyama Chemical Co., Ltd.); 2-[4-(3-Methyl-2-thienyl)phenyl]propionic acid derivs. and its non-toxic salts. DE 2850485; JP 1981049376 .
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) 51497 4'-Iodoacetophenone; 4-Iodoacetophenone; 1-(4-Iodophenyl)ethanone 13329-40-3 C8H7IO 详情 详情
(II) 10257 methyl 2-chloroacetate; methyl chloroacetate 96-34-4 C3H5ClO2 详情 详情
(III) 62683 methyl 3-(4-iodophenyl)-3-methyl-2-oxiranecarboxylate C11H11IO3 详情 详情
(IV) 62684 3-(4-iodophenyl)-3-methyl-2-oxiranecarboxylic acid C10H9IO3 详情 详情
(V) 62685 2-(4-iodophenyl)propanal C9H9IO 详情 详情
(VI) 62686   C18H16I2O4Zn 详情 详情
(VII) 12443 2-Bromo-3-methylthiophene 14282-76-9 C5H5BrS 详情 详情
(VIII) 36973 bromo(3-methyl-2-thienyl)magnesium C5H5BrMgS 详情 详情
(IX) 62687 2-[4-(3-methyl-2-thienyl)phenyl]propanoic acid C14H14O2S 详情 详情
(X) 10717 methyl (2S)-2-amino-2-phenylethanoate C9H11NO2 详情 详情
Extended Information