title: A new synthesis of phosphoramidates: inhibitors of the key bacterial enzyme aspartate semi-aldehyde dehydrogenase.
abstract: A new, mild and high yielding synthesis of phosphoramidates is described: potassium salts of carboxylic acids are treated with ethylchloroformate and the resulting activated anhydride-carbonates are then treated with LiNH-P(O)(OEt)2 in situ--the methodology is especially suited to acid sensitive systems featuring BOC, tBu or acetal protecting groups.
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D001223:Aspartate-Semialdehyde Dehydrogenase / Q000037:antagonists & inhibitors* / Q000737:chemistry; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism; D001665:Binding Sites; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D008958:Models, Molecular; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000577:Amides; D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D010756:Phosphoric Acids; C011067:phosphoramidic acid; D001223:Aspartate-Semialdehyde Dehydrogenase