Resolution of the enantiomers of tetrahydrozoline by chiral HPLC. The racemization of the enantiomers via an imine-enamine tautomerism

被引:11
作者
Caccamese, S [1 ]
Principato, G [1 ]
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
关键词
D O I
10.1016/S0957-4166(98)00300-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Resolution of the enantiomers of the sympathomimetic drug tetrahydrozoline was obtained by chiral HPLC. The isolated enantiomers racemize easily and chiral HPLC experiments allowed the determination of the racemization rate constant. This process occurs via an imine-enamine tautomerism which was studied by UV and H-1 NMR spectroscopies. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2939 / 2945
页数:7
相关论文
共 20 条
[1]  
AHLBRECHT H, 1969, TETRAHEDRON LETT, V6, P439
[2]  
ALLENMARK S, 1991, CHROMATOGRAPHIC ENAN, P51
[3]  
ARIENS EJ, 1990, RACEMIC TERAPEUTIC P, P29
[4]  
Blaha K., 1966, Adv. Heterocycl. Chem, V6, P147, DOI [10.1016/S0065-2725(08)60577-2, DOI 10.1016/S0065-2725(08)60577-2]
[5]   Separation of the enantiomers of anticonvulsant tricyclic pyrroloimidazolones by enantioselective HPLC. A chiral recognition model and a chiroptical study [J].
Caccamese, S ;
Principato, G ;
Chimirri, A ;
Grasso, S .
TETRAHEDRON-ASYMMETRY, 1996, 7 (09) :2577-2584
[6]   PIRKLE-CONCEPT CHIRAL STATIONARY PHASES FOR THE HPLC SEPARATION OF PHARMACEUTICAL RACEMATES [J].
CLEVELAND, T .
JOURNAL OF LIQUID CHROMATOGRAPHY, 1995, 18 (04) :649-671
[7]  
*COMM EUR COMM, 1992, INV CHIR ACT SUBST N
[8]  
ELIEL EL, 1962, STEREOCHEMISTRY CARB, P34
[9]  
*FDA, 1992, FDAS POL STAT DEV NE
[10]   COMPARISON OF CHEMICAL EXCHANGE RATES DETERMINED BY NUCLEAR MAGNETIC RESONANCE LINE-SHAPE AND EQUILIBRATION METHODS . INTERNAL ROTATION OF N-METHYL-N-BENZYLFORMAMIDE [J].
GUTOWSKY, HS ;
JONAS, J ;
SIDDALL, TH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4300-&