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

Abstract

A process for synthesizing 4-amino-2,4-dioxobutanoic acid involves reacting diethyl oxalate with an alkoxide 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-hydroxy-butenedioate, and afterward reacting the diethyl-2-cyano-3-hydroxy-butenedioate with an aqueous hydroxide under conditions suitable to form 4-amino-2,4-dioxobutanoic acid.

Inventors:
; ;
Issue Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1243346
Patent Number(s):
9290442
Application Number:
14/486,423
Assignee:
Los Alamos National Security, LLC (Los Alamos, NM) New Mexico Highlands University (Las Vegas, NM)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
DOE Contract Number:  
AC52-06NA25396
Resource Type:
Patent
Resource Relation:
Patent File Date: 2014 Sep 15
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES

Citation Formats

Unkefer, Pat J., Martinez, Rodolfo A., and Glass, David R.. Preparation of 4-amino-2,4-dioxobutanoic acid. United States: N. p., 2016. Web.
Unkefer, Pat J., Martinez, Rodolfo A., & Glass, David R.. Preparation of 4-amino-2,4-dioxobutanoic acid. United States.
Unkefer, Pat J., Martinez, Rodolfo A., and Glass, David R.. Tue . "Preparation of 4-amino-2,4-dioxobutanoic acid". United States. https://www.osti.gov/servlets/purl/1243346.
@article{osti_1243346,
title = {Preparation of 4-amino-2,4-dioxobutanoic acid},
author = {Unkefer, Pat J. and Martinez, Rodolfo A. and Glass, David R.},
abstractNote = {A process for synthesizing 4-amino-2,4-dioxobutanoic acid involves reacting diethyl oxalate with an alkoxide 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-hydroxy-butenedioate, and afterward reacting the diethyl-2-cyano-3-hydroxy-butenedioate with an aqueous hydroxide under conditions suitable to form 4-amino-2,4-dioxobutanoic acid.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2016},
month = {3}
}

Works referenced in this record:

Synthese von 1.5-Diaza-cyclooctan-dion-(4.8)-dicarbonsäure-(2.6)
journal, April 1954


An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions
journal, January 2007


Inhibition of cap (m7GpppXm)-dependent endonuclease of influenza virus by 4-substituted 2,4-dioxobutanoic acid compounds.
journal, December 1994


Utilization of the Amide Groups of Asparagine and 2-Hydroxysuccinamic Acid by Young Pea Leaves
journal, July 1984


Biological functions of proline in morphogenesis and osmotolerance revealed in antisense transgenic Arabidopsis thaliana
journal, April 1999


The Inactivation of Virus in Cultured Shoot Tips of Nicotiana rustica L.
journal, September 1969


Inhibitors of glycolic acid oxidase. 4-Substituted 3-hydroxy-1H-pyrrole-2,5-dione derivatives
journal, May 1983


Inhibitors of glycolic acid oxidase. 4-Substituted-2,4-dioxobutanoic acid derivatives
journal, August 1983


Improving the yield of plants
patent, July 1999


Effect of herbicides
patent, July 2000


Preparation of 2-hydroxy-5-oxoproline and analogs thereof
patent, September 2001


Withering-preventing and quick-acting nutrition supplementing agent for gramineous plants
patent, September 2002


Use of prolines for improving growth and other properties of plants and algae
patent, April 2003


Use of prolines for improving growth and other properties of plants and algae
patent, July 2003


Herbicide compositions comprising imidazolinone acid, methods of preparation, and methods of use
patent, March 2004


Agrochemical suspension formulations
patent, July 2004


Herbicide microemulsion-forming-concentrates, microemulsions, and methods
patent, October 2004


Use of prolines for improving growth and other properties of plants and algae
patent, December 2004


Herbicide composition comprising herbicide compound in acid form and acidifying agent
patent, June 2005


Herbicide microemulsion-forming-concentrates, microemulsions, and methods
patent, August 2006


Use of prolines for improving growth and/or yield
patent, October 2013


Herbicide composition comprising herbicide compound in acid form and acidifying agent
patent, June 2014


Use of prolines for improving growth and/or yield
patent, August 2014


Preparation of 4-amino-2,4-dioxobutanoic acid
patent, June 2015


Synthesis of 2-oxoglutaramate from L-glutamine
patent-application, February 2003


Use of prolines for improving growth and/or yield
patent-application, May 2007