58006-99-8

Usage

Also known as

dimethylmalic acid

Physical form

white crystalline solid

Taste

slightly sweet

Usage

food additive, flavoring agent, production of pharmaceuticals, chelating agent in metal ions

Potential properties

antimicrobial, antifungal

Upstream product

• 97-64-3 ethyl 2-hydroxypropionate 
• 624-83-9 methyl isocyanate 
• 58006-98-7 5-acetyl-3,5-dimethyl-oxazolidine-2,4-dione 
• 98336-19-7 (2-chloro-propionyl)-methyl-carbamic acid ethyl ester 
• 27770-23-6 5-methyl-2,4-oxazolidinedione 
• 74-88-4 methyl iodide 
• 4401-71-2 1,3-dimethylthymine 
• 69596-94-7 dl-trans-5-bromo-6-hydroxy-1,3-dimethyl-5,6-dihydrothymine 
• 124-38-9 carbon dioxide 
• 74538-22-0 α-bromo N-methyl propionamide 
• 17351-61-0 tetraethylammonium bicarbonate 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 127-48-0 trimethadione 
• 67535-04-0 3,5-dimethyl-5-(2-nitro-benzenesulfonyloxymethyl)-oxazolidine-2,4-dione 
• 67535-03-9 3,5-dimethyl-5-(toluene-4-sulfonyloxymethyl)-oxazolidine-2,4-dione 

Relevant academic research and scientific papers

Tetraethylammonium hydrogen carbonate in organic synthesis: Synthesis of oxazolidine-2,4-diones

Oxazolidine-2,4-diones were synthesised by tetraethylammonium hydrogen (TEAHC) promoted carboxylation of secondary carboxamides bearing a leaving group at the α-position. Several oxazolidine-2,4-diones, including clinically used malidone, have been prepared in moderate to excellent yields as a results of a formal proton extraction-carboxylation- intramolecular S(N)2 one-pot sequence.

Electrochemical Studies on Haloamides. Part XII. Electrosynthesis of Oxazolidine-2,4-diones

Electrogenerated bases promote the carboxylation of NH-protic carboxamides bearing a leaving group at the position 2 to give oxazolidine-2,4-diones.The process is believed to involve acid-base reaction with the substrate, carboxylation of its conjugate base to corresponding carbamate and ring-closure following intramolecular SN2 reaction.A variety of oxazolidine-2,4-diones, including clinically used trimethadione and malidone, have been prepared in high to excellent yield, which established the scope and generality of this new ring-forming process.

DIASTEREOSELECTIVE SYNTHESIS OF TRANS-4,5-DISUBSTITUTED OXAZOLIDIN-2-ONES AND VICINAL AMINO ALCOHOLS THROUGH ALKYLATION OF N-ACYLIMINIUM ION INTERMEDIATES

Treatment of 5-substituted 4-ethoxyoxazolidin-2-ones (10a-f, 13a,b) with allyltrimethylsilane in the presence of titanium tetrachloride gave the corresponding trans-4,5-disubstituted oxazolidin-2-ones (14a-f, 16a,b), respectively, with high diastereoselectivity.Methallylation of 13a,b with methallyltrimethylsilane yielded 16c,d, respectively.Ring cleavage of 14a-f afforded the corresponding threo vicinal amino alcohols 17a-f, respectively.

OXIDATION OF 1,3-DIMETHYL DERIVATIVES OF PYRIMIDINE BASES WITH m-CHLOROPERBENZOIC ACID

Oxidation of 1,3-dimethylthymine (1), 1,3-dimethyluracil (2), and 5-fluoro-1,3-dimethyluracil (3) with m-chloroperbenzoic acid were investigated. 1 gave the cis diol 5,6-dihydrothymine derivative (4) stereoselectively.Its stereostructure was definitely determined by an X-ray analysis. 2 afforded 7, 8, and 9, and 3 afforded 8.KEYWORDS - m-chloroperbenzoic acid oxidation; 1,3-dimethylthymine; 1,3-dimethyluracil; 5-fluoro-1,3-dimethyluracil; cis 5,6-dihydroxy-5,6-dihydrothymine