Separation of racemate hydrophobic thiourea substrates

Authors

  • Inas EL Hassan Laboratory of Applied Chemistry (LAC), Faculty of Science III, Lebanese University, P.O. Box 826, Tripoli
  • Fatm Houmaissi Laboratory of Applied Chemistry (LAC), Faculty of Science III, Lebanese University, P.O. Box 826, Tripoli
  • Mohammad Bouchekara Department of Chemistry, Faculty of Sciences and Technologies, University Mustapha Stanbouli of Mascara (29000)
  • Hanna El-Nakat Department of Chemistry, Faculty of Science, University of Balamand, P.O. Box 100, Tripoli
  • Fawaz El Omar Laboratory of Applied Chemistry (LAC), Faculty of Science III, Lebanese University, P.O. Box 826, Tripoli
  • Ahmad Khodr Allouch Laboratory of Applied Chemistry (LAC), Faculty of Science III, Lebanese University, P.O. Box 826, Tripoli,

DOI:

https://doi.org/10.7439/ijpc.v6i3.2931

Abstract

The separation of racemic-N-(2-ethylphenyl)-N'-(2-methylphenyl) thiourea, a hydrophobic substrate trap, to collect its atropisomers, was studied using reversed-phase high-performance liquid chromatography (RP-HPLC). Hydroxypropyl-beta-cyclodextrin (HP-?-CD) was used as a complexing additive to the racemic mixture (to obtain chiral molecules) and hexane-ethanol (50% in volume) as a mobile phase. The effects of mobile phase composition, on separation were systematically investigated to establish the optimum conditions of resolution.

Downloads

Download data is not yet available.

Author Biography

  • Ahmad Khodr Allouch, Laboratory of Applied Chemistry (LAC), Faculty of Science III, Lebanese University, P.O. Box 826, Tripoli,
    Department of Chemistry, Professor

References

Dalko P I and Moisan L, Angew Chem Int., 2004, 43(39), 5138-5175.

Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chemical Review. 98(5); 1998: 1743-1753.

Szem

Weseloh G, Bartsch H. and K

Arnaud S, Varesio E, Dreux M, and Veuthey J.L. Binding constant dependency of amphetamines with various commercial methylated-beta-cyclodextrins. Electrophoresis., 20 (13); 1999: 2670-2679.

Szem

Hermansson J. and von Bahr C. Simultaneous determination of dand l-Propranolol in human plasma by high-performance liquid chromatography. Journal of Chromatography B. 221 (1); 1980: 109

Hermansson J. Separation and quantification of (R)- and (S)-propranolol as their diastereomeric derivatives in human plasma by reversed-phase ion-pair chromatography. Acta Pharmceutica Suecica. 19 (1), 1982: 11

Thompson JA, Holtzman JL, Tsuru M. and Lerman CL. Procedure for the chiral derivatization and chromatographyc resolution of R-(+)- and S-(?)-propranolol. Journal of Chromatography A. 238(2); 1982: 470

Matsuo N. and Ohno N. Preparation of optically active 1-acetoxy-2-aryloxypropionitriles and its application to a facile synthesis of (S)-(?)-propranolol. Tetrahedron Letters. 26 (45); 1985: 5533

Terao Y, Murata M, Achiwa K, Nishino T, Akamatsu M. and Kamimura M. Highly efficient lipase-catalyzed asymmetric synthesis of chiral glicerol derivatives leading to practical synthesis of S-propranolol. Tetrahedron Letters. 29 (40); 1988: 5173

Szejtli J, Chem Rev., 1998, 98(5), 1743-1754.

a) Loftsson T and Brewster M E, J Pharm Sci., 1996, 85(10), 1017-1025; b) El Hassan I, Allouch A, Abou Dalle A, Tabcheh M, El-Nakat H and El Omar F, Asian J Res Chem., 2012, 5(6), 718-721

Uekama K, Hirayama F and Irie T, Chem Rev., 1998, 98(5), 2045-2076.

Szejtli J, Cyclodextrins and their inclusion complexes, Akademiai Kiad

Rajewski R A and Stella V J, J Pharm Sci., 1996, 85(11), 1142-1169.

Irie T and Uekama K, J Pharm Sci., 1997, 86(2), 147-162.

Bellec N, Lorcy D and Robert A, Synthesis, 1998, 10, 1442-1446, doi: 10.1055/s-1998-2183.

Lamparczyk H, and Zarzycki PK. The influence of temperature on the multiple separation of estrogenic steroids using mobile phases modified with _-cyclodextrin in high-performance liquid chromatography. Journal of Chromatography A. 668 (2), 1994: 413

Tarkanyi G. Quantitative approach for the screening of cyclodextrins by nuclear magnetic resonance spectroscopy in support of chiral separations in liquid chromatography and capillary electrophoresis enantioseparation of norgestrel with alpha-, beta- and gamma-cyclodextrins. Journal of Chromatography A. 961 (2), 2002: 257

Downloads

Published

2016-03-30

Issue

Section

Research Articles

How to Cite

1.
Separation of racemate hydrophobic thiourea substrates. Int J of Pharm Chem [Internet]. 2016 Mar. 30 [cited 2026 Jan. 4];6(3):87-91. Available from: https://ssjournals.co.in/index.php/ijpc/article/view/2931