IP Library Granted Patent US 9,045,392
Granted Patent B2
US 9,045,392 · App. 13/828,905 · Granted Jun 2, 2015

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

Inventors: Pat J. Unkefer (Los Alamos, NM); Rodolfo A. Martinez (Santa Fe, NM); David R. Glass (Las Vegas, NM)
Assignees: Los Alamos National Security, LLC; New Mexico Highlands University
C07C253/30C07C231/06
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Quick Facts
Patent No.
US 9,045,392
App. No.
13/828,905
Granted
Jun 2, 2015
Kind
B2
Abstract

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.

Claims (27)

1. A process for synthesizing 4-amino-2,4-dioxobutanoic acid, comprising:

reacting diethyl oxalate with sodium alkoxide in a suitable alcohol solvent 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,

isolating said first reaction product,

reacting said first reaction product with aqueous sodium hydroxide under conditions suitable to form 4-amino-2,4-dioxobutanoic acid.

2. A process for synthesizing 4-amino-2,4-dioxobutanoic acid, comprising:

reacting diethyl oxalate with sodium alkoxide in a first suitable solvent to form a reaction mixture, and afterward

adding ethyl cyanoacetate to the reaction mixture, and afterward

extracting the reaction mixture with a suitable organic solvent and water to form an organic layer and an aqueous layer, then

separating the aqueous layer from the organic layer, then

acidifying the aqueous layer and extracting the acidified aqueous layer with additional suitable organic solvent to form a second aqueous layer and a second organic layer, then

combining the first and second organic layers, and

isolating diethyl-2-cyano-3-hydroxy-butenedioate from the organic layers, then

reacting the diethyl-2-cyano-3-hydroxy-butenedioate with aqueous sodium hydroxide under conditions suitable to form 4-amino-2,4-dioxobutanoic acid.

3. The process of claim 2 , wherein the suitable organic solvent for extracting the reaction mixture is dichloromethane.

4. The process of claim 1 wherein said suitable alcohol solvent is ethanol.

5. The process of claim 2 wherein said first suitable solvent is ethanol.

6. The process of claim 3 wherein said first suitable solvent is ethanol.

7. The process of claim 1 wherein said sodium alkoxide is sodium ethoxide.

8. The process of claim 2 wherein said sodium alkoxide is sodium ethoxide.

9. The process of claim 3 wherein said sodium alkoxide is sodium ethoxide.

10. The process of claim 4 wherein said sodium alkoxide is sodium ethoxide.

11. The process of claim 5 wherein said sodium alkoxide is sodium ethoxide.

12. The process of claim 6 wherein said sodium alkoxide is sodium ethoxide.

13. The process of claim 7 wherein said suitable alcohol solvent is ethanol.

14. The process of claim 8 wherein said first suitable solvent is ethanol.

15. The process of claim 9 wherein said first suitable solvent is ethanol.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2018
From: LOS ALAMOS NATIONAL SECURITY, LLC
To: TRIAD NATIONAL SECURITY, LLC
Reel/Frame 047485/0471 →
CONFIRMATORY LICENSE Recorded Nov 27, 2015
From: LOS ALAMOS NATIONAL SECURITY
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 037148/0791 →
CONFIRMATORY LICENSE Recorded May 29, 2015
From: LOS ALAMOS NATIONAL SECURITY
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 035738/0883 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2015
From: MARTINEZ, RODOLFO A.; GLASS, DAVID R.
To: NEW MEXICO HIGHLANDS UNIVERSITY
Reel/Frame 035519/0311 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 26, 2013
From: UNKEFER, PAT J.
To: LOS ALAMOS NATIONAL SECURITY, LLC
Reel/Frame 031080/0043 →
Continuity (1)
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