A novel chiral polymer for enantioselective separation and process for preparation thereof
AssigneeCouncil of Scientific and Industrial Research
InventorsThangaraj Senthilkumar, Shyama Kumari Asha
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Abstract
The present invention relates to a novel polyfluorene appended with protected glutamic acid of Formula (I) for heterogeneous enantioselective separation and sensing of amino acids, amino alcohol, hydroxyl acid, sugar, aromatic drug and ascorbic acid from racemic mixture in water and process for preparation thereof. The present invention further provides a process for separation of enantiomers and diastereomers into their individual isomers using a polyfluorene compounds of Formula (I).
Claims7
A novel chiral polymer of Formula (I)
- wherein R is dicarboxylic amino acid, n indicates the repeating units of value ranging from 1-25, Molecular weight=25,400;
- dispersity index=1.7
A process of preparation of polymer of Formula I comprising the steps of:
- a) preparing a reaction mixture of 2,7-dibromofluorene, 6-bromohexan-1-ol and tetrabutyl ammonium chloride in toluene or DMSO.
- b) adding sodium hydroxide to the reaction mixture of step (a) followed by heating the mixture at the temperature ranging from 120° C. to 130° C. under argon atmosphere for 12 to 20 h to afford 2,7-dibromo-9,9-di-n-hexanolfluorene;
- c) esterifying 2,7-dibromo-9,9-di-n-hexanolfluorene using 4-dimethyl amino pyridine and boc-L-glutamic acid-1-tert butyl ester in presence of dicyclohexylcarbodiimide to afford (S)-1-tert-butyl-5-(6-(2,7-dibromo-9-(6-(((R)-5-(tert-butoxy)-4-((tert-butoxycarbonyl)amino)-5- oxopentanoyl)oxy)hexyl)-9H-fluoren-9-yl)hexyl)2-((tert-butoxycarbonyl)amino)pentanedioate;
- d) adding potassium carbonate to the reaction mixture comprising product of step (c), 1,4-benzene diboronic ester and Pd(PPh3)4 in THF followed by refluxing at a temperature ranging from 65° C. to 70° C. for 35 to 40 h to afford poly((S)-1-tert-butyl-5-(6-(9-(6-(((R)-5-(tert-butoxy)-4-((tert-butoxycarbonyl) amino)-5 -oxopentanoyl)oxy)hexyl)-9H-fluoren-9-yl)hexyl)2-((tert-butoxycarbonyl)amino)pentanedioate)(PF-GAP).
Dependencies are inferred from the claim text.