Wei Hui-qian
2015
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Chemical Reagents
Abstract
Research and optimize the chiral resolution of racemic 2-hydroxy-3-methoxy-3,3-diphenyl-propionic acid to obtain its single S-isomer. As a chiral resolving agent,( S)-1-( 4-Nitro-phenyl)-ethylamine hydrochloride salifys with 2-hydroxy-3-methoxy-3,3-diphenyl-propionic acid and generates a couple of diastereoisomers,which can be separated by their different solubility in solution. Acidize the diastereoisomer intermediate to obtain the product( S)-2-hydroxy-3-methoxy-3,3-diphenyl-propionic acid. The amount of solvent,resolving agent,acidscavenger,recrystallization condition and the chiral resolving agent's reclamation have been investigated. With 100 g racemic 2-hydroxy-3-methoxy-3,3-diphenyl-propionic acid as start material,in the condition of 20 equivalent of ethanol as solvent,1. 5 equivalent of triethylamine as acidscavenger and 0. 75 equivalent of solving agent,the resolution obtains the best yield( 40. 6%) and optical purity( 82. 8% e. e.),which can reachthe quality requirement( e. e. 99. 00%) after further recrystallization. With the advantages of simple in process,low-cost of raw materials and high-quality of product,the chiral resolution is suitable for industrial production.