36061-00-4

Usage

Uses

Used in Pharmaceutical Research:
Methyl 2-Acetamido-2-phenylacetate is employed as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs for the treatment of a range of diseases and conditions. Its unique structure and properties make it a valuable asset in medicinal chemistry.
Used in Organic Synthesis:
In the realm of organic synthesis, Methyl 2-Acetamido-2-phenylacetate is utilized as a building block for the preparation of a multitude of organic compounds. Its versatility in forming different chemical entities makes it an indispensable component in the synthesis of complex organic molecules.
Used in Medicinal Chemistry Development:
Methyl 2-Acetamido-2-phenylacetate is used as a precursor in the development of novel therapeutic agents, particularly in the field of medicinal chemistry. Its potential applications in the creation of new drugs highlight its importance in advancing pharmaceutical research and innovation.
Used in Chemical Industry:
Within the chemical industry, Methyl 2-Acetamido-2-phenylacetate is leveraged for its ability to form a variety of chemical compounds, playing a crucial role in the synthesis of specialty chemicals and intermediates for various applications.

Upstream product

• 67-56-1 methanol 
• 52068-22-1 α-Acetylamino-α-methylthiophenylessigsaeure-methanthiolester 
• 186541-36-6 (E)-N-(1,3-diphenylprop-2-en-1-yl)acetamide 
• 75-36-5 acetyl chloride 
• 24461-61-8 phenylglycine methyl ester 
• 15028-40-7 DL-2-phenylglycine methyl ester hydrochloride 
• 171181-53-6 methyl N^α-(diphenylmethylene)-DL-phenylglycinate 
• 1594106-38-3 N-(methoxy(phenyl)methyl)-N-(4-methoxybenzyl)acetamide 
• 60-35-5 acetamide 
• 22979-35-7 Methyl phenyldiazoacetate 
• 108-22-5 Isopropenyl acetate 
• 100-47-0 benzonitrile 
• 52068-21-0 1-Methansulfinyl-1-methylthio-2-amino-2-phenylethylen 
• 2835-06-5 phenylglycin 

Downstream Products

• 14257-84-2 (R)-(-)-N-acetylphenylglycine 
• 36060-85-2 (R)-N-acethylphenylglycine methyl ester 
• 14257-84-2 (S)-N-acetyl-2-phenylglycine 
• 100508-77-8 2-(Acetylimino)-2-phenylessigsaeure-methylester 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 100508-84-7 2-(Acetylamino)-2-hydroxy-2-phenylessigsaeure-methylester 
• 14257-84-2 N-acetyl-α-phenylglycine 
• 2835-06-5 phenylglycin 

Relevant academic research and scientific papers

A chiral cobalt(II) complex catalyzed asymmetric formal [3+2] cycloaddition for the synthesis of 1,2,4-triazolines

A highly efficient catalytic asymmetric formal [3+2] cycloaddition reaction of 5-alkoxyoxazoles with azodicarboxylate compounds has been realized by a chiral N,N′-dioxide/Co(BF4)2·6H2O complex. A series of poly-substituted 1,2,4-triazolines compounds were obtained in moderate to excellent yields (70-99%) with excellent enantioselectivities (82-98% ee).

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Synthesis of arylglycines from CO2 through α-amino organomanganese species

In the presence of three readily available chemicals, Mn powder, BF 3·OEt2, and LiCl, N-acyl-N,O-acetals were successfully converted into the corresponding α-amino acids (arylglycine derivatives) under 1 atm of a CO2 atmosphere in high yields. The LiCl additive is necessary in order to increase the solubility and the nucleophilicity of an organomanganese intermediate. The products thus obtained were transformed into free α-amino acids in two steps.

Iridium porphyrin catalyzed N-H insertion reactions: Scope and mechanism

Ir(TTP)CH3 catalyzed N-H insertion reactions between ethyl diazoacetate (EDA) or methyl phenyldiazoacetate (MPDA) and a variety of aryl, aliphatic, primary, and secondary amines to generate substituted glycine esters with modest to high yields. Aniline substrates generally gave yields above 80%, with up to 105 catalyst turnovers, and without slow addition of the diazo reagent. Good yields were also achieved with aliphatic amines, though higher catalyst loadings and slow addition of the amine were necessary in some cases. Primary amines reacted with EDA to generate both single- and double-insertion products, either of which could be produced selectively in high yield with the proper choice of stoichiometric ratios and reaction temperature. Notably, mixed trisubstituted amines, RN(CH2CO2Et) (CHPhCO2Me), were generated from the insertion of 1 equiv of EDA and 1 equiv of MPDA into primary amines. The N-H insertion mechanism was examined using substrate competition studies, trapping experiments, and multiple spectroscopic techniques. Substrate competition studies using pairs of amines with EDA or MPDA revealed Hammett correlations with respective slopes of ρ = 0.15 and ρ+ = -0.56 as well as kinetic isotope ratios of k H/kD = 1.0 ± 0.2 and 2.7 ± 0.2. Competitive amine binding to the iridium center was demonstrated by kinetics and equilibrium binding studies. Equilibrium binding constants ranged from 102 to 105. Monitoring the reaction by absorption spectroscopy revealed a transient metalloporphyrin complex. The lifetime of this species was dependent on the nature of the amine substrate, which suggests that the catalytic cycle proceeds through a metal-ylide intermediate.

Benzimidazole and imidazole inhibitors of histone deacetylases: Synthesis and biological activity

A series of N-hydroxy-3-[3-(1-substituted-1H-benzoimidazol-2-yl)-phenyl]-acrylamides (5a-5ab) and N-hydroxy-3-[3-(1,4,5-trisubstituted-1H-imidazol-2-yl)-phenyl]-acrylamides (12a-s) were designed, synthesized, and found to be nanomolar inhibitors of human histone deacetylases. Multiple compounds bearing an N1-piperidine demonstrate EC50s of 20-100 nM in human A549, HL60, and PC3 cells, in vitro and in vivo hyperacetylation of histones H3 and H4, and induction of p21waf. Compound 5x displays efficacy in human tumor xenograft models.

Preparation of N-acetyl-2-arylglycin esters by N-H insertion reaction of aryldiazoacetates with acetamide

The intermolecular N-H insertion reaction of methyl α-diazo α-arylacetate with acetamide has been investigated using transition-metal complexes as catalysts. The Cu(II) complex Cu(hfacac)2 (hfacac represents hexafluoroacetylacetonate) has prove

Acyl transfer catalysis with 1,2,4-Triazole anion

1,2,4-Triazole anion has been identified as an active acyl transfer catalyst suitable for the aminolysis and transesterification of esters.

A convenient protocol for C-H oxidation mediated by an azido radical culminating in Ritter-type amidation

Cerium(IV) ammonium nitrate in combination with sodium azide reacts with unactivated hydrocarbons in acetonitrile to furnish acetamides in one pot. The strategy can be used to introduce nitrogen functionality into a variety of compounds; a carboxylic ester directly afforded the corresponding α-amino acid.

Microwave-assisted rapid and simplified hydrogenation

Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 °C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 °C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of β-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters. Cleavage of the β-lactam ring by hydrogenolysis of the N-C4 bond of 4- aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.

Palladium-catalysed asymmetric allylic substitution: Synthesis of α- and β-amino acids

Methodology has been established for the formation of enantiomerically enriched α-amino acids using palladium-catalysed allylic amination. The formation of enantiomerically enriched allylamines has been achieved with high enantioselectivity. Oxidative cleavage of the allylamines provides arylglycine and glutamic acid derivatives. Additionally, enantiomerically enriched β-amino acids have been prepared in high enantiomeric excess. Palladium-catalysed asymmetric allylic substitution is used as the key synthetic transformation.