CuI-catalyzed coupling reaction of beta-amino acids or esters with aryl halides at temperature lower than that employed in the normal Ullmann reaction. Facile synthesis of SB-214857.
[reaction: see text] The CuI-catalyzed coupling reaction of aryl halides with beta-amino acids or beta-amino esters is completed at 100 degrees C in 48 h, which indicates that the structure of the beta-amino acid has an accelerating effect for the Ullmann-type aryl amination reaction. This coupling reaction can be used to prepare enantiopure N-aryl beta-amino acids. An efficient synthetic route to SB214857, a potent GPIIb/IIIa receptor antagonist, is developed using this method.
Ma
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State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, 354 Fenglin Lu, Shanghai 200032, China. madw@pub.sioc.ac.cn
Xia
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D000596:Amino Acids / Q000737:chemistry*; D001569:Benzodiazepines; D002384:Catalysis; D003300:Copper; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis*; D019039:Platelet Glycoprotein GPIIb-IIIa Complex / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
D000596:Amino Acids; D006846:Hydrocarbons, Halogenated; D010880:Piperidines; D019039:Platelet Glycoprotein GPIIb-IIIa Complex; D001569:Benzodiazepines; D003300:Copper; C412702:lotrafiban