Preparation of 4-amino-2,4-dioxobutanoic acid

Unkefer, Pat J.; Martinez, Rodolfo A.; Glass, David R.

Preparation of 4-amino-2,4-dioxobutanoic acid

Patent · Tue Jun 02 04:00:00 EDT 2015

OSTI ID:1183457

Unkefer, Pat J.; Martinez, Rodolfo A.; Glass, David R.

A process for synthesizing 4-amino-2,4-dioxobutanoic acid involves reacting diethyl oxalate with sodium ethoxide in ethanol to form a reaction mixture, and afterward adding ethyl cyanoacetate to the reaction mixture and allowing a reaction to proceed under conditions suitable to form a first reaction product of the formula diethyl-2-cyano-3-hydroxy-butenedioate, and then isolating the diethyl-2-cyano-3-hydroxybutenedioate, and afterward reacting the diethyl-2-cyano-3-hydroxy-butenedioate with aqueous sodium hydroxide under conditions suitable to form 4-amino-2,4-dioxobutanoic acid.

Research Organization:: Los Alamos National Laboratory (LANL), Los Alamos, NM (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC52-06NA25396

Assignee:: Los Alamos National Security, LLC (Los Alamos, NM)

Patent Number(s):: 9,045,392

Application Number:: 13/828,905

OSTI ID:: 1183457

Country of Publication:: United States

Language:: English

References (8)

An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions Verbic, Tatjana; Drakulic, Branko; Zloh, Mire Journal of the Serbian Chemical Society, Vol. 72, Issue 12 https://doi.org/10.2298/JSC0712201V	journal	January 2007
Inhibitors of glycolic acid oxidase. 4-Substituted 3-hydroxy-1H-pyrrole-2,5-dione derivatives Rooney, C. S.; Randall, W. C.; Streeter, K. B. Journal of Medicinal Chemistry, Vol. 26, Issue 5 https://doi.org/10.1021/jm00359a015	journal	May 1983
The Inactivation of Virus in Cultured Shoot Tips of Nicotiana rustica L. Walkey, D. G. A.; Fitzpatrick, J.; Woolfitt, J. M. G. Journal of General Virology, Vol. 5, Issue 2 https://doi.org/10.1099/0022-1317-5-2-237	journal	September 1969
Biological functions of proline in morphogenesis and osmotolerance revealed in antisense transgenic Arabidopsis thaliana Nanjo, Tokihiko; Kobayashi, Masatomo; Yoshiba, Yoshu The Plant Journal, Vol. 18, Issue 2, p. 185-193 https://doi.org/10.1046/j.1365-313X.1999.00438.x	journal	April 1999
Inhibitors of glycolic acid oxidase. 4-Substituted-2,4-dioxobutanoic acid derivatives Williams, H. W. R.; Eichler, E.; Randall, W. C. Journal of Medicinal Chemistry, Vol. 26, Issue 8 https://doi.org/10.1021/jm00362a020	journal	August 1983
Inhibition of cap (m7GpppXm)-dependent endonuclease of influenza virus by 4-substituted 2,4-dioxobutanoic acid compounds. Tomassini, J.; Selnick, H.; Davies, M. E. Antimicrobial Agents and Chemotherapy, Vol. 38, Issue 12 https://doi.org/10.1128/AAC.38.12.2827	journal	December 1994
Utilization of the Amide Groups of Asparagine and 2-Hydroxysuccinamic Acid by Young Pea Leaves Ta, Trung Chanh; Joy, Kenneth W.; Ireland, Robert J. Plant Physiology, Vol. 75, Issue 3 https://doi.org/10.1104/pp.75.3.527	journal	July 1984
Synthese von 1.5-Diaza-cyclooctan-dion-(4.8)-dicarbonsäure-(2.6) Weygand, Friedrich; Dietrich, Heinz-Jürgen Chemische Berichte, Vol. 87, Issue 4, p. 482-488 https://doi.org/10.1002/cber.19540870408	journal	April 1954

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