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Optical resolution by preferential crystallization of (2 RS, 3 SR )‐2‐amino‐3‐chlorobutanoic acid hydrochloride
Author(s) -
Shiraiwa Tadashi,
Miyazaki Hideya,
Ohta Atsushi,
Motonaka Kohji,
Kobayashi Etsuko,
Kubo Motoki,
Kurokawa Hidemoto
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:7<656::aid-chir3>3.0.co;2-5
Subject(s) - chemistry , hydrochloride , solubility , crystallization , triethylamine , chirality (physics) , yield (engineering) , resolution (logic) , optical rotation , amino acid , melting point , crystallography , chromatography , stereochemistry , organic chemistry , biochemistry , chiral symmetry breaking , physics , materials science , quantum mechanics , artificial intelligence , computer science , nambu–jona lasinio model , metallurgy , quark
(2 RS, 3 SR )‐2‐Amino‐3‐chlorobutanoic acid hydrochloride [(2 RS, 3 SR )‐ACB · HCl] was found to exist as a conglomerate based on the melting point, infrared spectrum, and solubility. Optical resolution by preferential crystallization of (2 RS, 3 SR )‐ACB · HCl was achieved to yield both (2 R, 3 S )‐ and (2 S, 3 R )‐ACB · HCl of 80–100% optical purities. The obtained (2 R, 3 S )‐ and (2 S, 3 R )‐ACB · HCl were recrystallized, taking into account the solubility of (2 RS, 3 SR )‐ACB · HCl, to give efficiently optically pure (2 R, 3 S )‐ and (2 S, 3 R )‐ACB · HCl. Treatment of the purified (2 R, 3 S )‐ and (2 S, 3 R )‐ACB · HCl with triethylamine gave optically pure (2 R, 3 S )‐ and (2 S, 3 R )‐2‐amino‐3‐chlorobutanoic acid, respectively. Chirality 9:656–660, 1997. © 1997 Wiley‐Liss, Inc.