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

【结 构 式】

【分子编号】56150

【品名】3-(2-Chlorophenyl)propionic acid

【CA登记号】1643-28-3

【 分 子 式 】C9H9ClO2

【 分 子 量 】184.62196

【元素组成】C 58.55% H 4.91% Cl 19.2% O 17.33%

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:(XVI)

In an alternative procedure, alkylation of diethyl malonate with 2-chlorobenzyl chloride (XIV) afforded malonate (XV), which underwent hydrolysis and further decarboxylation to the arylpropionic acid (XVI) upon refluxing with HCl and HOAc. Coupling of acid (XVI) with the chiral amine (III) to give amide (XVII) was performed in refluxing toluene with azeotropic removal of water or, alternatively, by using DCC as the coupling reagent. Amide (XVII) was finally reduced to the corresponding amine by means of borane in tetrahydrofuran or with DIBAL in CH2Cl2.

1 Yamazaki, N.; et al.; Nucleophilic addition of methyllithium to chiral oxime ethers: Asymmetric preparation of 1-(aryl)ethylamines and application to a synthesis of calcimimetics (+)-NPS R-568 and its thio analogue. Tetrahedron Lett 2001, 42, 30, 5029.
2 D'Ambra, T.E.; Vanwagenen, B.C.; Duff, S.R.; Nelson, W.A. (NPS Pharmaceuticals, Inc.); Method of making a benzylpropanamine. WO 9602492 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(III) 56140 (R)-1-(3-Methoxyphenyl)ethylamine; (R)-3-Methoxy-alpha-methylbenzylamine; (R)-m-Methoxy-alpha-methylbenzylamine 88196-70-7 C9H13NO 详情 详情
(XIV) 10205 1-Chloro-2-(chloromethyl)benzene; 2-Chlorobenzyl chloride 611-19-8 C7H6Cl2 详情 详情
(XV) 56149 diethyl 2-(2-chlorobenzyl)malonate C14H17ClO4 详情 详情
(XVI) 56150 3-(2-Chlorophenyl)propionic acid 1643-28-3 C9H9ClO2 详情 详情
(XVII) 56151 3-(2-chlorophenyl)-N-[(1R)-1-(3-methoxyphenyl)ethyl]propanamide C18H20ClNO2 详情 详情
Extended Information