Synthesis of Heterocyclic Analogs of α‐aminoadipic Acid and its Esters Based on Imidazo[2,1‐b][1,3]Thiazole |
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| Authors: | Algirdas ?a?kus Diana Bri?kut? Osvaldas Paliulis Frank Abildgaard Sløk |
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| Institution: | 1. Department of Organic Chemistry, Kaunas University of Technology, Kaunas, Lithuania;2. Institute of Synthetic Chemistry, Kaunas University of Technology, Kaunas, Lithuania;3. Vipergen ApS, Copenhagen, Denmark |
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| Abstract: | A method for the preparation of heterocyclic analogs of α‐aminoadipic acid and its esters based on the imidazo2,1‐b]1,3]thiazole ring system was developed. In this method, free‐radical bromination of ethyl 6‐methylimidazo2,1‐b]1,3]thiazole‐5‐carboxylate with NBS afforded a versatile building block, ethyl 6‐bromomethylimidazo2,1‐b]1,3]thiazole‐5‐carboxylate. Coupling of ethyl 6‐bromomethylimidazo2,1‐b]1,3]thiazole‐5‐carboxylate with Schöllkopf's chiral auxiliary followed by acidic hydrolysis generated ethyl 6‐(2S)‐2‐amino‐3‐methoxy‐3‐oxopropyl]imidazo2,1‐b]1,3]thiazole‐5‐carboxylate. A similar procedure using diethyl (Boc‐amino)malonate yielded racemic 2‐amino‐3‐(5‐ethoxycarbonyl)imidazo2,1‐b]1,3]thiazol‐6‐yl]propanoic acid. |
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