Analytical and semipreparative high performance liquid chromatography enantioseparation of new substituted 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)-pyrazoles on polysaccharide-based chiral stationary phases in normal-phase, polar organic and reversed-phase conditions.
The direct HPLC enantioseparation of five pairs of new chiral pyrazole derivatives on coated cellulose- and amylose-based chiral stationary phases (Chiralpak AD, Chiralcel OJ and Chiralcel OJ-RH) and new immobilised amylose-based Chiralpak IA CSP was performed. Very high enantioselectivity factor (alpha) values were achieved in polar organic and reversed-phase conditions by using OJ-RH as CSP. Chiralpak IA exhibited an excellent chiral resolving ability in normal-phase mode and it allowed the enantioseparation of analytes investigated with resolution factors (Rs) >20. Due to its bonded nature, it was successfully employed at analytical and semipreparative scale in combination with normal-phase eluents containing "non-standards" solvents such as acetone.
Cirilli
R
R
Istituto Superiore di Sanità, Dipartimento del Farmaco, Viale Regina Elena 299, 00161 Rome, Italy. rcirilli@iss.it
Simonelli
A
A
Ferretti
R
R
Bolasco
A
A
Chimenti
P
P
Secci
D
D
Maccioni
E
E
La Torre
F
F
D000688:Amylose / Q000031:analogs & derivatives; D001565:Benzoates; D002482:Cellulose / Q000031:analogs & derivatives; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D048448:Phenylcarbamates; D011720:Pyrazoles / Q000302:isolation & purification*; D012997:Solvents; D013237:Stereoisomerism
D001565:Benzoates; D048448:Phenylcarbamates; D011720:Pyrazoles; D012997:Solvents; C090722:tris(4-methylbenzoate)cellulose; C080033:Chiralpak AD; D002482:Cellulose; D000688:Amylose