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

页码：1879 / 1884

页数：6

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 [J].

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 .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4462-4470

[2] NEW ASYMMETRIC TRANSFORMATION OF ALPHA-AMINO-ACID ESTERS WITH (+)-TARTARIC ACID [J].

CLARK, JC ;

PHILLIPPS, GH ;

STEER, MR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (05) :475-481

[3] Strategies in optical resolution:: a practical guide [J].

Faigl, Ferenc ;

Fogassy, Elemer ;

Nogradi, Mihaly ;

Palovics, Emese ;

Schindler, Jozsef .

TETRAHEDRON-ASYMMETRY, 2008, 19 (05) :519-536

[4] Synthesis and stereochemical stability of new atropisomeric 1-(substituted phenyl)pyrrole derivatives [J].

Faigl, Ferenc ;

Tarkanyi, Gabor ;

Fogassy, Katalin ;

Tepfenhardt, Dora ;

Thurner, Angelika .

TETRAHEDRON, 2008, 64 (07) :1371-1377

[5] Efficient synthesis and resolution of (±)-1-[2-carboxy-6-(trifluoromethyl)phenyl]pyrrole-2-carboxylic acid [J].

Fogassy, K ;

Harmat, V ;

Böcskei, Z ;

Tárkányi, G ;

Toke, L ;

Faigl, F .

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 [J].

GAVEZZOTTI, A ;

FILIPPINI, G .

JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (18) :4831-4837

[7] ARE CRYSTAL-STRUCTURES PREDICTABLE [J].

GAVEZZOTTI, A .

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 [J].

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 .

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 [J].

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. .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2008, 41 :466-470

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