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Optical resolution by preferential crystallization of (2RS,3SR)-2-amino-3-chlorobutanoic acid hydrochloride
Authors:Tadashi Shiraiwa  Hideya Miyazaki  Atsushi Ohta  Kohji Motonaka  Etsuko Kobayashi  Motoki Kubo  Hidemoto Kurokawa
Abstract:(2RS,3SR)-2-Amino-3-chlorobutanoic acid hydrochloride (2RS,3SR)-ACB · HCl] was found to exist as a conglomerate based on the melting point, infrared spectrum, and solubility. Optical resolution by preferential crystallization of (2RS,3SR)-ACB · HCl was achieved to yield both (2R,3S)- and (2S,3R)-ACB · HCl of 80–100% optical purities. The obtained (2R,3S)- and (2S,3R)-ACB · HCl were recrystallized, taking into account the solubility of (2RS,3SR)-ACB · HCl, to give efficiently optically pure (2R,3S)- and (2S,3R)-ACB · HCl. Treatment of the purified (2R,3S)- and (2S,3R)-ACB · HCl with triethylamine gave optically pure (2R,3S)- and (2S,3R)-2-amino-3-chlorobutanoic acid, respectively. Chirality 9:656–660, 1997. © 1997 Wiley-Liss, Inc.
Keywords:β  -chloro-α  -amino acid  conglomerate  successive optical resolution  racemic structure  (2RS  3SR)-ACB ·  HCl
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