10304-09-3

Usage

Uses

Used in Chemical Synthesis:
Methoxy(oxo)acetic acid is used as a key intermediate in the synthesis of various organic compounds, facilitating the production of a range of industrial and consumer products.
Used in Herbicide Production:
Methoxy(oxo)acetic acid is utilized as a precursor in the manufacturing process of certain herbicides, contributing to their effectiveness in controlling unwanted plant growth.
Used in Dye Manufacturing:
In the dye industry, methoxy(oxo)acetic acid is employed as a chemical component in the production of dyes, enhancing their color properties and performance.
Used in Pharmaceutical Development:
Methoxy(oxo)acetic acid serves as a building block in the development of pharmaceuticals, playing a crucial role in the synthesis of various medicinal compounds.
Used as a Solvent:
Due to its solubility properties, methoxy(oxo)acetic acid is used as a solvent in various chemical processes, aiding in the dissolution and reaction of other substances.
Used in Polymer and Plastics Production:
Methoxy(oxo)acetic acid is incorporated in the manufacturing of polymers and plastics, contributing to their structural integrity and functional characteristics.
Used in Research and Development:
In scientific research, methoxy(oxo)acetic acid is employed as a reagent or starting material in various experimental procedures, advancing the understanding of chemical reactions and the development of new compounds.

Synthetic route

Dimethyl oxalate (553-90-2) → potassium oxalate monomethyl ester (10304-09-3)

Conditions	Yield
With potassium acetate In methanol; water at 80℃; for 3h;	100%
With potassium acetate In methanol; water at 80℃; for 3h;	91%
With potassium acetate In methanol; water at 60℃; for 1h;	80%
With potassium acetate In methanol; water at 90℃; for 2h; Reflux;

potassium oxalate monomethyl ester (10304-09-3) + (2R)-2,3-diaminopropanoic acid monohydrochloride (1482-97-9, 6018-55-9, 6018-56-0, 19777-68-5, 19777-69-6, 28843-13-2, 54897-59-5, 69531-11-9, 125767-61-5) → β-N-oxalyl-D-α,β-diaminopropionic acid

Conditions	Yield
Stage #1: (2R)-2,3-diaminopropanoic acid monohydrochloride With lithium hydroxide monohydrate In methanol; water for 1h; Cooling with ice; Stage #2: potassium oxalate monomethyl ester In methanol; water at 20℃; for 18h; Concentration;	77%

potassium oxalate monomethyl ester (10304-09-3) + 4-bromo-<2,3,5,6-2H4>anisole (152404-45-0) → C9H6(2)H4O3

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; palladium dichloride In 1-methyl-pyrrolidin-2-one at 150℃; for 24h; Inert atmosphere; Schlenk technique;	75%

triphenylplumbyl hydroxide (894-08-6) + potassium oxalate monomethyl ester (10304-09-3) → (C6H5)3PbO2CCO2CH3 (107399-19-9)

Conditions	Yield
With methanol In methanol HO2CCO2CH3 prepared in situ from potassium salt in methanol, pptd. at room temp. by equimolar amount of R3MOH; suspn. in CH3OH warmed, solvent vol. reduced; elem. anal.;	74%

potassium oxalate monomethyl ester (10304-09-3) + Trimethylbleimonohydroxyd (17546-98-4) → (CH3)3PbO2CCO2CH3 (107399-17-7)

Conditions	Yield
With methanol In methanol HO2CCO2CH3 prepared in situ from potassium salt in methanol, pptd. at room temp. by equimolar amount of R3MOH; suspn. in CH3OH warmed, solvent vol. reduced; elem. anal.;	70%

triphenyltin(IV) hydroxide (76-87-9) + potassium oxalate monomethyl ester (10304-09-3) → (C6H5)3SnO2CCO2CH3 (107399-18-8)

Conditions	Yield
With methanol In methanol HO2CCO2CH3 prepared in situ from potassium salt in methanol, pptd. at room temp. by equimolar amount of R3MOH; suspn. in CH3OH warmed, solvent vol. reduced; elem. anal.;	65%

potassium oxalate monomethyl ester (10304-09-3) + trimethyltin(IV) hydroxide (56-24-6) → (CH3)3SnO2CCO2CH3 (107399-16-6)

Conditions	Yield
With methanol In methanol HO2CCO2CH3 prepared in situ from potassium salt and methanol, pptd. at room temp. by equimolar amount R3MOH; suspn. in CH3OH warmed, solvent vol. reduced; elem. anal.;	56%

para-bromotoluene (106-38-7) + potassium oxalate monomethyl ester (10304-09-3) → 4-methyl-benzoic acid methyl ester (99-75-2)

Conditions	Yield
With palladium(II) trifluoroacetate; 1,3-bis-(diphenylphosphino)propane In 1-methyl-pyrrolidin-2-one at 150℃; for 24h; Inert atmosphere;	52%

Ethyl 2-bromohexanoate (615-96-3) + potassium oxalate monomethyl ester (10304-09-3) → 1-ethoxy-1-oxohexan-2-yl methyl oxalate

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 48h; Inert atmosphere;	49%

monomethyl oxalyl chloride (5781-53-3) + potassium oxalate monomethyl ester (10304-09-3) → methoxalic anhydride (5781-55-5)

Conditions	Yield
(i) aq. KOAc, MeOH, (ii) /BRN= 1071541/, benzene,; Multistep reaction;

menadione (58-27-5) + potassium oxalate monomethyl ester (10304-09-3) → 2,3-dimethyl[1,4]naphthoquinone (2197-57-1)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

menadione (58-27-5) + potassium oxalate monomethyl ester (10304-09-3) → 3-methyl-1,4-dioxo-1,4-dihydronaphthalene-2-carboxylic acid methyl ester (68749-80-4)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

menadione (58-27-5) + potassium oxalate monomethyl ester (10304-09-3) → 2-Methyl-1,4-dioxo-1,2,3,4-tetrahydro-naphthalene-2,3-dicarboxylic acid dimethyl ester (68749-81-5)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

3-Bromojuglone (52431-65-9) + potassium oxalate monomethyl ester (10304-09-3) → 2-Methoxycarbonyl-3-bromjuglon (68749-89-3)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

2-benzyl-1,4-naphthoquinone (33440-68-5) + potassium oxalate monomethyl ester (10304-09-3) → 2‐benzyl‐3‐methylnaphthalene‐1,4‐dione (52711-59-8)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

2-benzyl-1,4-naphthoquinone (33440-68-5) + potassium oxalate monomethyl ester (10304-09-3) → 2-Benzyl-3-methoxycarbonyl-1.4-naphthochinon

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

potassium oxalate monomethyl ester (10304-09-3) + [1,4]naphthoquinone (130-15-4) → 2,3-dimethoxycarbonyl-1,4-naphthoquinone (68749-78-0)

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate In acetonitrile

1H-imidazole (288-32-4) + potassium oxalate monomethyl ester (10304-09-3) → α-oxo-1H-imidazole-1-acetic acid, methyl ester (72030-76-3)

Conditions	Yield
With oxalyl dichloride; methanesulfonic acid 1.) acetonitrile, RT, 5 min, 2.) acetonitrile, RT, 20 min; Yield given. Multistep reaction;

potassium oxalate monomethyl ester (10304-09-3) + (R)-2-tert-butoxycarbonyl-3-aminopropionic acid (73259-81-1, 113625-76-6, 76387-70-7) → β-N-oxalyl-D-α,β-diaminopropionic acid

Conditions	Yield
Stage #1: (R)-2-tert-butoxycarbonyl-3-aminopropionic acid With water; lithium hydroxide In methanol at 0 - 5℃; for 0.666667h; pH=Ca. 8; Stage #2: potassium oxalate monomethyl ester In methanol; water at 0 - 20℃; for 20h;	930 g

Upstream product

• 553-90-2 Dimethyl oxalate 

Downstream Products

• 5781-55-5 methoxalic anhydride 
• 107399-19-9 (C₆H₅)3PbO₂CCO₂CH₃ 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 107399-18-8 (C₆H₅)3SnO₂CCO₂CH₃ 
• 52711-59-8 2‐benzyl‐3‐methylnaphthalene‐1,4‐dione 

Relevant academic research and scientific papers

Preparation and plant growth-regulatory activity of N'-substituted N- furfuryloxamides

N'-Substituted N-furfuryloxamides (4) were prepared via condensation of potassium methyl oxalate (8) with furfurylamine (5f) using 1,1'- oxalyldiimidazole (6), followed by hydrolysis of the resulting amide-ester (10), and finally condensation with aliphatic or aromatic amines (5). The prepared compounds (4) were examined for activity as plant growth regulators using two kinds of plant seeds, namely, those of rape, Brassica campestris L. (Dicotyledoneae) and leek, Allium tuberosum ROTTLER (Monocotyledoneae). N'- Benzyl- and N'-phenyl-N-furfuryloxamides (4b and 4c) and N,N'- difurfuryloxamide (4f) inhibited root growth in seedlings of both species.

Preparation method and application of D-dencichine

The invention discloses a preparation method and application of D-dencichine. The preparation method comprises the following steps: carrying out Fmoc protection on the amino group of D-asparagine so as to obtain a first intermediate; subjecting the first intermediate to Hoffman degradation reaction so as to obtain a second intermediate; subjecting the second intermediate to removal of Fmoc protection under the action of organic base so as to obtain a third intermediate; and subjecting the third intermediate and monomethyl oxalate to condensation reaction under a highly basic condition so as to obtain D-dencichine. D-dencichine is prepared by using the high-efficiency safe preparation method; the preparation method is simple and has high yield; the compound D-dencichine prepared by using the method has good treatment effect on thrombocytopenia and the effect is better than the effect of a clinical medicine interleukin-11, so D-dencichine can be used as a candidate medicine for treating thrombocytopenia.

METHODS OF NAD+-DEPENDENT DEACETYLASE INHIBITORS

The present invention relates to methods of treating cancer, cardiovascular disorders, and neurological disorders using NAD+-dependent deacetylase inhibitors.