Resolution of 1-[2-carboxy-6-(trifluoromethyl)phenyl]-1H-pyrrole-2-carboxylic acid with methyl (R)-2-phenylglycinate, reciprocal resolution and second order asymmetric transformation

被引：22
作者：
Faigl, Ferenc [1 ,2 ]
Matravoelgyi, Bela [2 ]
Holczbauer, Tamas [3 ]
Czugler, Matyas [3 ]
Madarasz, Janos [4 ]
机构：
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1111 Budapest, Hungary
[2] Hungarian Acad Sci, Organ Chem Technol Res Grp, H-1111 Budapest, Hungary
[3] Hungarian Acad Sci, Inst Struct Chem, H-1025 Budapest, Hungary
[4] Budapest Univ Technol & Econ, Dept Gen & Analyt Chem, H-1111 Budapest, Hungary
来源：
TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 20-22期
基金：
匈牙利科学研究基金会;
关键词：
CRYSTAL-STRUCTURES; DERIVATIVES;
D O I：
10.1016/j.tetasy.2011.10.021
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A novel, highly efficient method has been developed for the separation of the optical isomers of 1-[2-carboxy-6-(trifluoromethyl)phenyl]-1H-pyrrole-2-carboxylic acid with methyl (R)-2-phenylglycinate. The structural aspects of chiral discrimination have been discussed via comparison of the molecular structures and the packing energies of the diastereoisomeric salts determined by single crystal X-ray diffraction measurements. Reciprocal resolution and a new, highly efficient second order asymmetric transformation of racemic methyl 2-phenylglycinate with the pure enantiomer of the previously resolved atropisomeric carboxylic acid are also reported. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1879 / 1884
页数：6
相关论文
共 16 条
  • [1] Pyrrolobenzoxazepinone derivatives as non-nucleoside HIV-1 RT inhibitors: Further structure-activity relationship studies and identification of more potent broad-spectrum HIV-1 RT inhibitors with antiviral activity
    Campiani, G
    Morelli, E
    Fabbrini, M
    Nacci, V
    Greco, G
    Novellino, E
    Ramunno, A
    Maga, G
    Spadari, S
    Caliendo, G
    Bergamini, A
    Faggioli, E
    Uccella, I
    Bolacchi, F
    Marini, S
    Coletta, M
    Nacca, A
    Caccia, S
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) : 4462 - 4470
  • [2] NEW ASYMMETRIC TRANSFORMATION OF ALPHA-AMINO-ACID ESTERS WITH (+)-TARTARIC ACID
    CLARK, JC
    PHILLIPPS, GH
    STEER, MR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (05): : 475 - 481
  • [3] Strategies in optical resolution:: a practical guide
    Faigl, Ferenc
    Fogassy, Elemer
    Nogradi, Mihaly
    Palovics, Emese
    Schindler, Jozsef
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (05) : 519 - 536
  • [4] Synthesis and stereochemical stability of new atropisomeric 1-(substituted phenyl)pyrrole derivatives
    Faigl, Ferenc
    Tarkanyi, Gabor
    Fogassy, Katalin
    Tepfenhardt, Dora
    Thurner, Angelika
    [J]. TETRAHEDRON, 2008, 64 (07) : 1371 - 1377
  • [5] Efficient synthesis and resolution of (±)-1-[2-carboxy-6-(trifluoromethyl)phenyl]pyrrole-2-carboxylic acid
    Fogassy, K
    Harmat, V
    Böcskei, Z
    Tárkányi, G
    Toke, L
    Faigl, F
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (23) : 4771 - 4780
  • [6] GEOMETRY OF THE INTERMOLECULAR X-H...Y (X, Y=N, O) HYDROGEN-BOND AND THE CALIBRATION OF EMPIRICAL HYDROGEN-BOND POTENTIALS
    GAVEZZOTTI, A
    FILIPPINI, G
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (18) : 4831 - 4837
  • [7] ARE CRYSTAL-STRUCTURES PREDICTABLE
    GAVEZZOTTI, A
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (10) : 309 - 314
  • [8] Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis
    Genin, MJ
    Allwine, DA
    Anderson, DJ
    Barbachyn, MR
    Emmert, DE
    Garmon, SA
    Graber, DR
    Grega, KC
    Hester, JB
    Hutchinson, DK
    Morris, J
    Reischer, RJ
    Ford, CW
    Zurenko, GE
    Hamel, JC
    Schaadt, RD
    Stapert, D
    Yagi, BH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) : 953 - 970
  • [9] Lopata A., 1984, J. Chem. Res., V14, P322
  • [10] Mercury CSD 2.0 -: new features for the visualization and investigation of crystal structures
    Macrae, Clare F.
    Bruno, Ian J.
    Chisholm, James A.
    Edgington, Paul R.
    McCabe, Patrick
    Pidcock, Elna
    Rodriguez-Monge, Lucia
    Taylor, Robin
    van de Streek, Jacco
    Wood, Peter A.
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2008, 41 : 466 - 470
12