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

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

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

Issue Date:: 2016-03-22

OSTI Identifier:: 1243345

Assignee:: Los Alamos National Security, LLC (Los Alamos, NM) New Mexico Highlands University (Las Vegas, NM) LANL

Patent Number(s):: 9,290,443

Application Number:: 14/489,329

Contract Number:: AC52-06NA25396

Resource Relation:: Patent File Date: 2014 Sep 17

Research Org:: Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Sponsoring Org:: USDOE

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES

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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

Nanjo, Tokihiko; Kobayashi, Masatomo; Yoshiba, Yoshu
The Plant Journal, Vol. 18, Issue 2, p. 185-193
DOI: 10.1046/j.1365-313X.1999.00438.x

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

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