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  • 1
    Electronic Resource
    Electronic Resource
    Optical resolution by preferential crystallization of DL-methionine hydrochloride (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 48-51 
    Details
    ISSN: 0899-0042
    Keywords: amino acid ; successive optical resolution ; conglomerate ; binary phase diagram ; racemic structure ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: DL-Methionine hydrochloride (DL-Met·HCl) was found to exist as a conglomerate, based on the infrared spectrum, solubility, and melting point. The optical resolution of DL-Met·HCl was successfully achieved by preferential crystallization into D-and L-Met·HCl. Treatment of the purified D- and L-Met·HCl with triethylamine gave D- and L-methionine of 100% optical purities. Chirality, 9;48-51, 1997. © 1997 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
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  • 2
    Electronic Resource
    Electronic Resource
    Preparation and isolation of 2-methylamino-3-phenylpropanoic acid enantiomers using selective crystallization (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 386-389 
    Details
    ISSN: 0899-0042
    Keywords: optical resolution ; diastereomeric method ; molecular compound ; 2-chloro-3-phenylpropanoic acid ; 2-methylamino-3-phenylpropanoic acid ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: First, (RS)-2-chloro-3-phenylpropanoic acid [(RS)-CPP] was optically resolved using ethyl (S)-phenylalaninate as a resolving agent, aiming at preparation of optically active 2-methylamino-3-phenylpropanoic acid (MPP). The (R)-CPP obtained as the sodium salt monohydrate was reacted with methylamine to give (S)-2-methylamino-3-phenylpropanoic acid [(S)-MPP]. Next, the optical resolution of (RS)-MPP was also attempted via molecular compound formation with optically active mandelic acid (MAN). The molecular compound of (R)-MPP with (S)-MAN [(R)-MPP (S)-MAN] was obtained as the less soluble diastereomeric compound, while the (S)-MPP (S)-MAN compound was found to be the more soluble one. Recrystallization of (R)-MPP (S)-MAN compound from water, followed by treatment with acetone, gave optically pure (R)-MPP in 79% yield, based on a half amount of the starting (RS)-MPP. The (S)-MPP obtained from (S)-MPP (S)-MAN compound was again subjected to formation of molecular compound with (R)-MAN to give optically pure (S,)-MPP in 66% yield. Chirality 9:386-389, 1997. © 1997 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
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  • 3
    Electronic Resource
    Electronic Resource
    Successive optical resolution by replacing crystallization of DL-threonine (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 6 (1994), S. 654-657 
    Details
    ISSN: 0899-0042
    Keywords: successive optical resolution ; replacing crystallization ; threonine ; optically active cosolute ; L-serine ; 4-hydroxy-L-proline ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: DL-Threonine [DL-Thr; (2RS,3SR)-2-amino-3-hydroxybutanoic acid] was optically resolved by replacing crystallization using L-serine (L-Ser) and 4-hydroxy-L-proline (L-Hyp) as optically active cosolutes. D-Thr was allowed to crystallize preferentially from racemic aqueous solutions in the presence of these L-α-amino acids. The optical resolution of DL-Thr was more successfully achieved by using L-Ser, whose structure is more similar to that of DL-Thr than L-Hyp, and successively gave D- and L-Thr of 87 - 92% optical purities. The D- and L-Thr obtained were then recrystallized from water to give optically pure D- and L-Thr. © 1994 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530060809
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  • 4
    Electronic Resource
    Electronic Resource
    Optical resolution by preferential crystallization of (RS)-2-amino-3-chloropropanoic acid hydrochloride (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 197-200 
    Details
    ISSN: 0899-0042
    Keywords: optical resolution ; conglomerate ; preferential crystallization ; optically active 2-amino-3-chloropropanoic acid ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The racemic structures of (RS)-2-amino-3-chloropropanoic acid [(RS)-ACP] and (RS)-2-amino-3-chloropropanoic acid hydrochloride [(RS-ACP·HCl] were examined to obtain (R)- and (S)-ACP via optical resolution by preferential crystallization. The melting point, infrared spectrum, solubility, and ternary solubility diagram suggested that (RS)-ACP·HCl exists as a conglomerate and that (RS)-ACP forms a racemic compound. Optical resolution by preferential crystallization of (RS)-ACP·HCl was successfully achieved to yield (R)- and (S)-ACP·HCl. Optically pure (R)- and (S)-ACP were obtained from the purified (R)-and (S)-ACP·HCl, respectively. © 1996 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
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  • 5
    Electronic Resource
    Electronic Resource
    Optical resolution by preferential crystallization of (2RS,3SR)-2-amino-3-chlorobutanoic acid hydrochloride (1997)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 656-660 
    Details
    ISSN: 0899-0042
    Keywords: β-chloro-α-amino acid ; conglomerate ; successive optical resolution ; racemic structure ; (2RS,3SR)-ACB · HCl ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (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.
    Additional Material: 4 Ill.
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  • 6
    Electronic Resource
    Electronic Resource
    Optical resolution by preferential crystallization of 4-methylpiperidinium hydrogen (RS)-phenylsuccinate (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 6 (1994), S. 202-206 
    Details
    ISSN: 0899-0042
    Keywords: optical resolution ; successive preferential crystallization ; phenylsuccinic acid ; organic ammonium hydrogen phenylsuccinates ; racemic structure ; free enrgey of racemate formation ; binary melting point diagram ; ternary solubility diagram ; free energy of critical nucleation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Gibbs energy of racemate formation, binary melting point diagram, and ternary solubility diagram suggested that 4-piperidinium hydrogen (RS)-phenylsuccinate [(RS)-4-MP salt] exists in a conglomerate. Appropriate conditions were explored on the basis of free energy of critical nucleation in a supersaturated solution to resolve efficiently (RS)-4-MP salt by preferential crystallization. Successive preferential crystallization of (RS)-4-MP salt in ethanol at 20°C gave (R)- and (S)-4-MP salts of 90-94% optical purities. Optically pure (R)- and (S)-phenylsuccinic acids were obtained by recrystallization of the (R)- and (S)-4-MP salts, followed by treatment of the salts purified with hydrochloric acid. © 1994 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530060307
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