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Royal Society of Chemistry, CrystEngComm, 5(15), p. 931-939

DOI: 10.1039/c2ce26706c

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Salts of (+)-deoxycholic acid with amines: Structure, thermal stability, kinetics of salt formation, decomposition and chiral resolution

This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

(+)-Deoxycholic acid forms salts with 1-propylamine, di-n-butylamine, sec-butylamine and 3-methyl-2-butylamine. The salts were characterised using thermal analysis and single crystal X-ray diffraction. The chiral discrimination of (+)-deoxycholic acid for racemic sec-butylamine and racemic 3-methyl-2-butylamine was studied and correlated with the structural and thermal results. A mixture of (+)-deoxycholic acid and racemic sec-butylamine yielded crystals of (R)-2-butylammonium deoxycholate. (+)-Deoxycholic acid was exposed to vapours of propylamine and racemic sec-butylamine and the kinetics of absorption were determined. The kinetics of decomposition of powdered samples obtained from (+)-deoxycholic acid with di-n-butylamine and racemic sec-butylamine were investigated. Crystallisation of (+)-deoxycholic acid with racemic 3-methyl-2-butylamine resulted in crystals of (S)-3-methyl-2-butylammonium deoxycholate.