YAKHAK HOEJI (약학회지)

The Pharmaceutical Society of Korea (대한약학회)
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Synthesis of $(\pm)-\alpha-Hydroxy-\alpha$-(p-Chlorobiphenyl)Acetic Acid and its Resolution

$(\pm)-\alpha-Hydroxy-\alpha$-(p-Chlorobiphenyl)acetic acid 합성과 분할

  • Published : 1995.08.01
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Abstract

Optically pure(-)-and (+)-$\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)acetic acids were prepared. The racemate was synthesized through three steps. By condensation of p-cnorobiphenyl with diethyl ketomalonate in the presence of SnCl$_{4}$, diethyl $\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)malonate (1) was formed and subsequently ($\pm$)-$\alpha$-hydroxy-$\alpha$-(p-chlorobiphenyl)acetic acid (3) was obtained through hydrolysis and decarboxylation. For the separation of the racemate the classical resolution method, derivatization of a racemate by reaction with an optically pure compound was employed. In this case the optically pure compound were [R]-(+)-$\alpha$-methylbenzylamine and [S]-(-)-$\alpha$-methylbenzylamine. Diastereomeric salts between acids and bases could be easily separated by crystallization in absolute ethanol.

Keywords

References

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