Resolution of (±)-mandelic- and (±)-2-(chlorophenoxy)propionic-acid derivatives by crystallization of their diastereomeric amides with (R)- or (S)-α-arylethylamines

被引:4
|
作者
Jourdain, F
Hirokawa, T
Kogane, T
机构
[1] Kanagawa Ind Technol & Res Inst, Fundamental Technol Div, Kanagawa 2430435, Japan
[2] Yokohama Natl Univ, Ctr Corp Res & Dev, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan
关键词
D O I
10.1016/S0040-4039(99)00169-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An alternative and cost effective route for the resolution in high ees (95-99%) of (+/-)-mandelic- and (+/-)-2-(chlorophenoxy)propionic- acid derivatives is reported. The key step involves the covalent derivatization and separation of their diastereomeric amides with (R)- or (S)-alpha-arylethylamines. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2307 / 2310
页数:4
相关论文
共 49 条
  • [22] Efficient access to N-protected derivatives of (R,R,R)- and (S,S,S)-octahydroindole-2-carboxylic acid by HPLC resolution
    Sayago, Francisco J.
    Jimenez, Ana I.
    Cativiela, Carlos
    TETRAHEDRON-ASYMMETRY, 2007, 18 (19) : 2358 - 2364
  • [23] Molecular requisites for drug binding to muscle CLC-1 and renal CLC- K channel revealed by the use of phenoxy-alkyl derivatives of 2-(p-chlorophenoxy)propionic acid
    Liantonio, A
    Accardi, A
    Carbonara, G
    Fracchiolla, G
    Loiodice, F
    Tortorella, P
    Traverso, S
    Guida, P
    Pierno, S
    De Luca, A
    Camerino, DC
    Pusch, M
    MOLECULAR PHARMACOLOGY, 2002, 62 (02) : 265 - 271
  • [24] Syntheses, characterizations, crystal structures, and in vitro antitumor activities of chiral triorganotin(IV) complexes containing (S)-(+)-2-(4-isobutyl-phenyl)propionic and (R)-(+)-2-(4-hydroxyphenoxy)propionic acid ligands
    Shi, Yang
    Zhang, Bao-Ying
    Zhang, Ru-Fen
    Zhang, Shao-Liang
    Ma, Chun-Lin
    JOURNAL OF COORDINATION CHEMISTRY, 2012, 65 (23) : 4125 - 4136
  • [25] RESOLUTION OF 2-(ALPHA-HYDROXYBENZYL)-1,4,5,6-TETRAHYDROPYRIMIDINES AND A COMPARISON OF THEIR OPTICAL ROTARY DISPERSION CURVES WITH THOSE OF RELATED MANDELIC ACID DERIVATIVES
    NEILSON, DG
    KHAN, IA
    WHITEHEA.RS
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (15): : 1853 - &
  • [26] Effect of ultrasound-assisted crystallization in the diastereomeric salt resolution of tetramisole enantiomers in ternary system with O,O′-dibenzoyl-(2R,3R)-tartaric acid
    Szeleczky, Zsolt
    Kis-Mihaly, Erzsebet
    Semsey, Sandor
    Pataki, Hajnalka
    Bagi, Peter
    Palovics, Emese
    Marosi, Gyorgy
    Pokol, Gyorgy
    Fogassy, Elemer
    Madardsz, Janos
    ULTRASONICS SONOCHEMISTRY, 2016, 32 : 8 - 17
  • [27] Enantioselective Resolution of (R, S)-2-Phenoxy-Propionic Acid Methyl Ester by Covalent Immobilized Lipase from Aspergillus oryzae
    Weichao Zhong
    Mengjie Zhang
    Xiaojun Li
    Yinjun Zhang
    Zhao Wang
    Jianyong Zheng
    Applied Biochemistry and Biotechnology, 2020, 190 : 1049 - 1059
  • [28] Enantioselective Resolution of (R, S)-2-Phenoxy-Propionic Acid Methyl Ester by Covalent Immobilized Lipase from Aspergillus oryzae
    Zhong, Weichao
    Zhang, Mengjie
    Li, Xiaojun
    Zhang, Yinjun
    Wang, Zhao
    Zheng, Jianyong
    APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 2020, 190 (03) : 1049 - 1059
  • [29] CEC enantioseparations on chiral monolithic columns:: A study of the stereoselective degradation of (R/S)-dichlorprop [2-(2,4-dichlorophenoxy)propionic acid] in soil
    Messina, Antonella
    Sinibaldi, Massimo
    ELECTROPHORESIS, 2007, 28 (15) : 2613 - 2618
  • [30] Genetic and phenotypic diversity of (R/S)-mecoprop [2-(2-methyl-4-chloropheno)propionic acid]-degrading bacteria isolated from soils
    Lim, JS
    Jung, MK
    Kim, MS
    Alm, JH
    Ka, JO
    JOURNAL OF MICROBIOLOGY, 2004, 42 (02) : 87 - 93