Acetyohydroxamic Acid
From The Cure For The Needy
Contents |
Acetohydroxamic Acid (AHA, Lithostat)
Effective Against
Acetohydroxamic Acid is a urease inhibitor. It works by decreasing ammonia levels and pH in the urine. This helps antibiotics to work better and decreases kidney stone formation
Cost
Cost of molecule from Sigma-Aldrich: 39.30 USD (5g)
Reported Routes of Synthesis
By reaction of ethyl acetate (I) with hydroxylamine hydrochloride in ethanol-water at alkaline pH.
Gangadhar, A.; Subbarao, R.; Lakshminara Yana, G. Reduction of unsaturated fatty acids and fatty alcohols with diimide from hydroxylamine-ethyl acetate. J Am Oil Chem Soc 1984, 61(7): 1239
Cost of Reagents:
Hydroxylamine hydrochloride from Sigma-Aldrich: 36.7 USD (5 g)
Ethyl acetate from Sigma-Aldrich: 28 USD (100 mL)
Acetohydroxamic acid can be prepared in several ways as follows: 1) Condensation of ethyl acetate (I) with NH2OH·HCl in the presence of KOH in MeOH furnishes potassium acetohydroxamate (II), which is then subjected to cation-exchange with Amberlite IRC-50 resin in the presence of HCl (1) 2) Basification of acetohydroxamic acid HCl salt (III) with NaHCO3 in H2O (2). 3) Treatment of N-acetyl imidazole (IV) with NH2OH·HCl in THF (3). 4) Reaction of 1-nitroethane (IV) with SeO2 in the presence of Et3N in CH2Cl2 (4). 5) Condensation of acetyl chloride (VI) with NH2OH in H2O (2).
Staab, H.A.; Lueking, M.; Duerr, F.H. Darstellung von imidazoliden. Synthese von amiden, hydraziden und hydroxamsäuren nach der imidazolidmethode Chem Ber 1962, 95(5): 1275
Sosnovsky, G.; Krogh, J.A. A new method for the preparation of aliphatic hydroxamic acids; Reaction of primary nitroalkanes with selenium dioxide in the presence of triethylamine Synthesis (Stuttgart) 1980, (8): 654
Wise, W.M.; Brandt, W.W. An investigation of some hydroxamic acids J Am Chem Soc 1955, 77(4): 1058
Morphochem AG. Hydroxamic acids as methionine-aminopeptidase (MAP) inhibitors DE 10256976