Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Racemic Structures of Organic Ammonium Salts of N-Acetyl-DL-2-aminobutyric Acid and N-Acetyl-DL-norvaline and Optical Resolution by Preferential Crystallization of DL-Ammonium Salts
Tadashi ShiraiwaHirokazu YoshidaMakoto TsudaHidemoto Kurokawa
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1987 Volume 60 Issue 3 Pages 947-952

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Abstract

The racemic structures of the ammonium salts (AM salts) and seven organic ammonium salts of N-acetyl-DL-2-aminobutyric acid (DL-AcAbu) and N-acetyl-DL-norvaline (DL-AcNva) were studied on the basis of thermodynamic analyses to explore the possibility of optical resolution by preferential crystallization. An empirical equation has been derived from thermodynamic data at melting points of ammonium and organic ammonium salts of N-acyl-DL-amino acids to predict racemic structures around room temperature. The AM salts of DL-AcAbu and -AcNva exist in conglomerate around room temperature. It is possible to resolve optically these DL-AM salts by preferential crystallization in ethanol at 10 °C, and the successive preferential crystallization followed by purification gave D- and L-2-aminobutyric acids and -norvalines with optical purities close to 100%.

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