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

Abstract

A process for synthesizing 4-amino-2,4-dioxobutanoate involves reacting a dialkyl oxalate with an alkoxide in ethanol to form a reaction mixture, and afterward adding an alkyl cyano acetate 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-dioxobutanoate. The 4-amino-2,4-dioxobutanoate may be acidified into 4-amino-2,4-dioxobutanoic acid.

Inventors:
; ;
Publication Date:
Research Org.:
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1243345
Patent Number(s):
9,290,443
Application Number:
14/489,329
Assignee:
Los Alamos National Security, LLC (Los Alamos, NM) New Mexico Highlands University (Las Vegas, NM) LANL
DOE Contract Number:  
AC52-06NA25396
Resource Type:
Patent
Resource Relation:
Patent File Date: 2014 Sep 17
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. doi:. https://www.osti.gov/servlets/purl/1243345.
@article{osti_1243345,
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-dioxobutanoate involves reacting a dialkyl oxalate with an alkoxide in ethanol to form a reaction mixture, and afterward adding an alkyl cyano acetate 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-dioxobutanoate. The 4-amino-2,4-dioxobutanoate may be acidified into 4-amino-2,4-dioxobutanoic acid.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Mar 22 00:00:00 EDT 2016},
month = {Tue Mar 22 00:00:00 EDT 2016}
}

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Works referenced in this record:

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

  • Weygand, Friedrich; Dietrich, Heinz-Jürgen
  • Chemische Berichte, Vol. 87, Issue 4, p. 482-488
  • DOI: 10.1002/cber.19540870408

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


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

  • Weygand, Friedrich; Dietrich, Heinz-Jürgen
  • Chemische Berichte, Vol. 87, Issue 4, p. 482-488
  • DOI: 10.1002/cber.19540870408