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Synthesis and Hydrophobic Properties of Benzoxazoles
* 1 , 2 , 1 , 1
1  Zentiva a. s., U kabelovny 130, 102 37 Prague 10, Czech Republic
2  Department of Inorganic and Organic Chemistry, Charles University in Prague, Faculty of Pharmacy in Hradec Kralove, 500 05 Hradec Kralove, Czech Republic

Abstract: A series of fourteen lipophilic 2-substituted 5,7-di-tert-butylbenzoxazoles was prepared by the reaction of 2-amino-4,6-di-tert-butylphenol with appropriated aldehydes. The general synthetic approach of all newly synthesized compounds is presented. All the substituted 5,7-di-tert-butylbenzoxazoles derivatives were analyzed using the reversed phase high performance liquid chromatography (RP-HPLC) method for the lipophilicity measurement. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using end-capped non-polar C18 stationary RP column. In the present study the correlation between RP-HPLC retention parameter Log K (the logarithm of capacity factor K) and various calculated Log P values is shown. The relationships between the lipophilicity and the chemical structure of the studied compounds are discussed as well.
Keywords: 2-amino-4,6-di-tert-butylphenol; 5,7-Di-tert-butylbenzoxazoles; Lipophilicity measurement; Structure-lipophilicity relationships2-amino-4,6-di-tert-butylphenol; 5,7-Di-tert-butylbenzoxazoles; lipophilicity measurement; structure-lipophilicity relationships