6293-20-5

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL UREIDOACETATE is used as a chemical intermediate for the synthesis of benzoylhydantoic acids by reacting with benzoic acids. This reaction is crucial in the preparation of various pharmaceutical compounds, as benzoylhydantoic acids are key components in the development of drugs with therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, ETHYL UREIDOACETATE is utilized as a versatile building block for the creation of a wide range of chemical compounds. Its urea and ester functional groups make it a valuable precursor in the synthesis of various organic molecules, including those with potential applications in materials science, agrochemicals, and other industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 2880, 1950 DOI: 10.1021/ja01163a019

Upstream product

• 64-17-5 ethanol 
• 462-60-2 N-carbamoylglycine 
• 590-28-3 potassium cyanate 
• 623-33-6 glycine ethyl ester hydrochloride 
• 556-89-8 nitrourea 
• 459-73-4 GlyOEt*HCl 
• 2949-22-6 Glycine ethyl ester isocyanate 
• 18873-00-2 N-(Phenylhydrazinocarbonyl)-glycinethylester 
• 57-13-6 urea 

Downstream Products

• 461-72-3 2,4-imidazolidinedione 
• 67792-85-2 3-nitroso-hydantoic acid ethyl ester 
• 614-22-2 1-benzoylurea 
• 95494-01-2 (4-amino-6-anilino-[1,3,5]triazin-2-ylmethyl)-urea 
• 96955-15-6 1,3-Bis-(N-ureidoacetyl-aminomethyl)-benzol 
• 43077-49-2 ethyl [3-(1-diphenoxyphosphinylbutyl)ureido]acetate 
• 98629-84-6 N-ethoxycarbonylmethylbarbituric acid 
• 89694-35-9 ethyl 2,4,5-trioxoimidazolidine-1-acetate 
• 462-60-2 N-carbamoylglycine 
• 1027543-34-5 ethyl 3-(2-nitrobenzyl)-2,4,5-trioxoimidazolidine-1-acetate 
• 303986-62-1 [3-(4-Nitro-benzyl)-2,4,5-trioxo-imidazolidin-1-yl]-acetic acid ethyl ester 
• 859967-38-7 5-(N-phenyl-glycyl)-hydantoic acid ethyl ester 
• 7684-19-7 N-[(phenylamino)carbonyl]glycine ethyl ester 
• 187160-64-1 ethyl 5-hydroxy-3-(3-nitrobenzyl)-2,4-dioxoimidazolidine-1-acetate 

Relevant academic research and scientific papers

An efficient multi-component synthesis of N-1-alkylated 5-nitrouracils from α-amino acids

The preparation of N-1 selectively alkylated uracil intermediates usually requires selective protection at N-3 followed by alkylation at N-1 and subsequent removal of the protecting group. In this Letter, we show the limitations of this approach when quaternary C centres at N-1 became a key target for the programme. To access this key substructure, we developed an efficient multi-component reaction (MCR) from readily available α-amino acid precursors.

Highly selective aldose reductase inhibitors. 1. 3-(Arylalkyl)-2,4,5- trioxoimidazolidine-1-acetic acids

A series of 3-(arylalkyl)-2,4,5-trioxoimidazolidine-1-acetic acids (1) was prepared and tested for aldose reductase (AR) and aldehyde reductase (ALR) inhibitory activities. These compounds showed strong inhibitory activity against AR without significant inhibitory activity for ALR. The ratio of IC50(ALR)IC50(AR) was > 1000 in some compounds. On the basis of pharmacological tests such as the recovery of reduced motor nerve conduction velocity and toxicological profile, 3-(3-nitrobenzyl)-2,4,5- trioxoimidazolidine-1-acetic acid (NZ-314) was selected as the candidate for clinical development.

BASE CATALYZED CYCLIZATION OF SUBSTITUTED ESTERS OF HYDANTOIC AND THIOHYDANTOIC ACID

Base catalyzed cyclization rates have been measured of 22 derivatives of hydantoic and thiohydantoic acid esters in water and methanol.The cyclization of methyl and ethyl esters of hydantoic and 5-methylhydantoic acids is accompanied by hydrolysis of the ester group, whereas with the other derivatives the hydrolysis does not take place.Hydrolysis of the cyclization products (hydantoin and thiohydantoin derivatives) is not significant under the kinetic conditions.The cyclization of methyl ester of 5-phenylhydantoic acid in methanol is reversible; the equilibrium mixture contains 30percent of the starting ester.In all the cases the cyclization is subject to specific base catalysis; exceptions are esters of 5-phenylthiohydantoic and 5-phenyl-2-methylthiohydantoic acids whose cyclizations are subject to general base catalysis.Substituents always accelerate the cyclization.The 3-substituents have the greatest effects, the cyclization rate being considerably increased with bulk of the substituents; similarly large effect of 5-phenyl group consists mainly in its polar effects on the pre-equilibrium.The cyclizations are slower in methanol at the same concentration of the lyate ion: the greatest difference (up to 3 orders of magnitude) is observed with the 5-phenyl derivatives.