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Preparation of Optically Active (2RS,3SR)-2-amino-3-hydroxy-3-phenylpropanoic Acid (Threo-Beta-Phenylserine) via Optical Resolutions by Replacing and Preferential Crystallization

Preparation of Optically Active (2RS,3SR)-2-amino-3-hydroxy-3-phenylpropanoic Acid (Threo-Beta-Phenylserine) via Optical Resolutions by Replacing and Preferential Crystallization

Tadashi Shiraiwa, Yuka Kawashima, Atsushi Ikaritani, Yumiko Suganuma, Reiichi Saijoh

Chem Pharm Bull (Tokyo). 2006 Aug;54(8):1170-4.

PMID: 16880663

Abstract:

To obtain optically active threo-2-amino-3-hydroxy-3-phenylpropanoic acid (1) via optical resolutions by replacing and preferential crystallization, the racemic structure of (2RS,3SR)-1 hydrochloride [(2RS,3SR)-1.HCl] was examined based on the melting point, solubility, and infrared spectrum. (2RS,3SR)-1.HCl was indicated to exist as a conglomerate at room temperature, although it forms a racemic compound at the melting point. When, in optical resolution by replacing crystallization, L-phenylalanine methyl ester hydrochloride (L-2) was used as the optically active co-solute, (2R,3S)-1.HCl was preferentially crystallized from the supersaturated racemic solution; the use of D-2 as the co-solute afforded (2S,3R)-1.HCl with an optical purity of 95%. In addition, optical resolution by preferential crystallization was successfully achieved to give successively (2R,3S)- and (2S,3R)-1.HCl with optical purities of 90-92%. The (2R,3S)- and (2S,3R)-1.HCl purified by recrystallization from 1-propanol were treated with triethylamine in methanol to give optically pure (2R,3S)- and (2S,3R)-1.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP17585692	L-Phenylalanine hydrochloride solution		17585-69-2	Price

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