52771-14-9

Usage

Uses

Used in Pharmaceutical Research and Development:
(Acetylamino)(4-methoxyphenyl)acetic acid is used as a potential therapeutic agent for [application reason] pain and inflammation-related conditions due to its analgesic and anti-inflammatory effects.
Used in Pain Management:
In the medical industry, (acetylamino)(4-methoxyphenyl)acetic acid is used as a potential treatment option for [application reason] managing pain associated with various conditions, given its analgesic properties.
Used in Inflammation Treatment:
(Acetylamino)(4-methoxyphenyl)acetic acid is also used as a potential treatment for [application reason] inflammation-related conditions, leveraging its anti-inflammatory effects.
Used in Drug Development:
In the pharmaceutical industry, (acetylamino)(4-methoxyphenyl)acetic acid is used as a potential drug candidate for [application reason] the management of various medical conditions, as its specific interactions and biological activities are still being studied and show promise.

Upstream product

• 18649-43-9 4-methoxyphenyllead(IV) triacetate 
• 162247-62-3 4-Ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one 
• 60-35-5 acetamide 
• 201230-82-2 carbon monoxide 
• 123-11-5 4-methoxy-benzaldehyde 
• 75-05-8 acetonitrile 
• 77648-21-6 ethyl 2-amino-2-(4-methoxyphenyl) acetate 
• 14062-18-1 ethyl p-methoxyphenylacetate 
• 77629-83-5 ethyl 2-bromo-2-(4-methoxyphenyl) acetate 
• 77629-84-6 (±)-ethyl 2-azido-2-(4-methoxyphenyl)acetate 
• 148000-82-2 2-acetamido-2-(4'-methoxyphenyl)acetate d'ethyle 
• 162247-68-9 4-(4-Methoxy-phenyl)-2-methyl-5-oxo-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester 

Downstream Products

• 24593-48-4 (2S)-2-amino-2-(4-methoxyphenyl)acetic acid 
• 869470-04-2 2-methyl-4-(p-methoxyphenyl)-4H-oxazolin-5-one 

Relevant academic research and scientific papers

Efficient ligand-free, palladium-catalyzed amidocarbonylation in ionic liquids: Facile synthesis of N-acyl-α-arylglycines

A ligand-free, palladium-catalyzed amidocarbonylation reaction of aromatic aldehyde, acetamide, and CO in ionic liquids [C4mim]PF6, [C6mim]PF6, [C8mim]PF6, and [C6mim]BF4 as solvents is developed. The yields decreased in the order [C6mim]PF6 > [C8mim]PF6 > [C4mim]PF6 > [C6mim]BF4, and substrate concentration affected the catalytic activity of amidocarbonylation. The excellent yield with up to 98% in amidocarbonylation of benzaldehyde was obtained using 15 mol% LiBr · H2O and 6 mol% H2SO4 at 80°C. This reaction could proceed smoothly, resulting in several functionalized ortho-, meta-, and para-substituted N-acyl-α-phenylglycines in moderate to good yields, and o-tolualdehyde and m-tolualdehyde as substrates were amidocarbonylated for the first time in [C6mim]PF6. A significant dependence of product yield on both substituent position and electronic effect of aromatic aldehyde was observed. The ligand-free synthetic method and convenient separation of the products highlighted the versatility of this newly developed methodology. Copyright Taylor & Francis Group, LLC.

METHOD OF AMIDOCARBONYLATION REACTION

A novel method of an amidocarbonylation reaction among an aldehyde compound, an amide compound, and carbon monoxide, which comprises using a palladium-supporting crosslinked-polymer composition containing palladium clusters having a major-axis length of 20 nm or shorter to conduct the amidocarbonylation reaction. Thus, an N-acyl-±-amino acid can be more efficiently and selectively synthesized in a clean reaction system. Also provided is a catalyst for use in the method.

Diastereochemical diversity of imidazoline scaffolds via substrate controlled TMSCI mediated cycloaddition of azlactones

(Chemical Equation Presented) We report herein a trimethylsilyl chloride mediated substrate controlled 1,3-dipolar cycloaddition for the diastereoselective synthesis of either syn- or anti-imidazolines. This method provides scaffolds with four points of diversity and control over two stereocenters.

Efficient synthesis of N-acyl-α-amino acids via polymer incarcerated palladium-catalyzed amidocarbonylation

A novel polymer incarcerated Pd catalyst (PI Pd 7c) was synthesized from amide-containing polymer 6b, and this catalyst was shown to be effective in amidocarbonylation, which is a versatile one-pot method for the preparation of N-acyl-α-amino acids. The reactions proceeded smoothly with a wide variety of substrates, and no leaching of the Pd metal to the reaction mixture was detected.

First amidocarbonylation with nitriles for the synthesis of N-acyl amino acids

A new and efficient one-pot synthesis of N-acyl-α-amino acids by amidocarbonylation is described. Starting from aldehydes, nitriles and carbon monoxide in the presence of acid and palladium catalysts the desired N-acyl amino acids are obtained in good yie

Efficient chemoenzymatic synthesis of enantiomerically pure α-amino acids

A general two-step chemoenzymatic synthesis for enantiomerically pure natural and nonnatural α-amino acids is presented. In the first step of the sequence, the ubiquitous educts aldehyde, amide and carbon monoxide react by palladium-catalyzed amidocarbonylation to afford the racemic N-acyl amino acids in excellent yields. In the second step, enzymatic enantioselective hydrolysis yields the free optically pure a-amino acid and the other enantiomer as the N-acyl derivative, both in optical purities of 85-99.5% ee. The advantage of the chemoenzymatic process compared to other amino acid synthesis are demonstrated by the preparation of various functionalized (-OR, -Cl, -F, -SR) α-amino acids on a 10-g scale.

Palladium-catalyzed amidocarbonylation - A new, efficient synthesis of N-acyl amino acids

For the first time palladium catalysts have been used successfully for the amidocarbonylation reaction. The activity of the cobalt catalysts that were used exclusively beforehand has now been exceeded by an order of magnitude, and the reaction can be performed under far milder conditions. Palladium-catalyzed amidocarbonylation reactions can now be used for the synthesis of a much wider range of N-acyl amino acids.

Reaction of organolead triacetates with 4-ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one. The synthesis of α-aryl- and α-vinyl-N-acetylglycines and their ethyl esters and their enzymic resolution

4-Ethoxycarbonyl-2-methyl-4,5-dihydro-1,3-oxazol-5-one 7, which may be readily obtained from diethyl acetamidomalonate, undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which may be hydrolysed to give either the α-aryl- or α-vinyl-N-acetylglycine or the corresponding ethyl ester. The kinetic resolution of a number of these derivatives by enzymic hydrolysis of either the amide or ester function has been demonstrated.

Reaction of Organolead Triacetates with 4-Ethoxycarbonyl-2-methyloxazol-5-one. The Synthesis of α-Aryl and α-Vinyl N-Acetylglycine Ethyl Esters and Their Enzymic Resolution.

An efficient synthesis of the moisture-sensitive compound, 4-ethoxycarbonyl-2-methyloxazol-5-one, has been achieved.This compound undergoes high-yielding arylation and vinylation at the 4-position with organolead triacetates to give compounds which in water are converted to α-aryl and α-vinyl N-acetylglycine ethyl esters.These α-substituted glycine derivatives may be kinetically resolved in very good yield and high enantiomeric excess by enzymic hydrolysis of either the ester group or the amide function of the corresponding carboxylic acids.