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Direct resolution of propranolol and bupranolol by thin-layer chromatography using cellulose derivatives as stationary phase

Suedee, R. and Heard, Charles Martin 1997. Direct resolution of propranolol and bupranolol by thin-layer chromatography using cellulose derivatives as stationary phase. Chirality -New York- 9 (2) , pp. 139-144. 10.1002/(SICI)1520-636X(1997)9:2<139::AID-CHIR11>3.0.CO;2-O

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Abstract

Cellulose triphenylcarbamate derivatives have been used as stationary phases for resolution of the enantiomers of the β-blockers propranolol and bupranolol by TLC. The derivatives examined were: cellulose trisphenylacarbamate (1), cellulose tris(2,3-dichlorophenyl carbamate) (2), cellulose tris(2,4-dichlorophenyl carbamate) (3), cellulose tris(2,6-dichlorophenyl carbamate) (4), cellulose tris (2,3-dimethylphenyl carbamate) (5), cellulose tris(3,4-dichlorophenyl carbamate) (6), cellulose tris(3,5-dichlorophenyl carbamate) (7), and cellulose tris(3,5-dimethylphenyl carbamate) (8). A variety of mobile phases were used to achieve useful separations and the effects of solvent polarity are also discussed. The best resolution of rac-propranolol was obtained on CSP 8 (RfR = 0.26, RfS = 0.06, α = 4.33) in mobile phase hexane:propan-2-ol (80:20 v/v). The best resolution of rac-bupranolol was obtained on CSP 5 (RfR = 0.29, RfS = 0.09, α = 3.22) in mobile phase hexane:propan-2-ol (80:20 v/v). These results demonstrated the potential of cellulose triphenylcarbamates as chiral stationary phases in TLC and indicate that this is potentially a useful method for the direct, simple, and rapid (within 30 min) resolution of racemates in the analytical control of enantiomeric purity. Physical aspects such as problems in cracking of the CSP, adhesion to plate, and interference of spot detection due to triphenylcarbamate chromphores are also discussed, along with the method employed to overcome them.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Subjects: R Medicine > RS Pharmacy and materia medica
Publisher: Wiley-Blackwell
ISSN: 0899-0042
Last Modified: 04 Jun 2017 07:44
URI: http://orca.cf.ac.uk/id/eprint/67511

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