Synthesis and Application of Novel Glyoxylate-derived Chloroformates

Autor:	Brian S. MacDougall, Ki Ho Chung, James C. Gallagher, Duyan V. Nguyen, Mark J. Mulvihill, William Dean Mathis, Damian Gerard Weaver
Rok vydání:	2002
Předmět:	Solvent system chemistry.chemical_compound chemistry Iodoacetic acid Triphosgene Organic Chemistry Pyridine Glyoxylate cycle Moiety Organic chemistry Thiocarbonate Chloroformate Catalysis
Zdroj:	Synthesis. 2002:365-370
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2002-20036
Popis:	A convenient process for the synthesis of glyoxylate-derived chloroformates has been developed. The approach involves the reaction of glyoxylate esters with triphosgene and pyridine in various solvent systems. These novelglyoxylate-derived chloroformates are multifunctional, possessing a chloroformate, ester, and haloalkyl moiety. Further elaboration via a thiocarbonate route afforded highly functionalized carboxylic acid-derived alkoxycarbonyl-chlorocarbonyloxy-methyl esters. Application of a benzyl glyoxylate-derived chloroformate to halofenozide was also accomplished, affording halofenozide-N-carbonyloxy-chloro/iodoacetic acid benzyl ester derivatives, which were further derivatized to carboxylic acid-derived (halofenozide-N-carbonyloxy)-benzyloxycarbonyl-methyl esters. The trifunctional nature of the glyoxylate moiety was demonstrated through conversion of the benzyloxycarbonyl moiety of a carboxylic acid-derived (halofenozide-N-carbonyloxy)-benzyloxycarbonyl-methyl ester to its respective diethylamide.
Databáze:	OpenAIRE
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