53612-87-6

Basic information

• Product Name: Propanedioic acid, (acetylamino)[(4-methoxyphenyl)methyl]-, diethyl ester
• CAS NO: 53612-87-6
• Molecular Formula: C17H23NO6
• Molecular Weight: 337.373
• Mol File: 53612-87-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, (acetylamino)[(4-methoxyphenyl)methyl]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, (acetylamino)[(4-methoxyphenyl)methyl]-, diethyl ester(53612-87-6)
• EPA Substance Registry System: Propanedioic acid, (acetylamino)[(4-methoxyphenyl)methyl]-, diethyl ester(53612-87-6)

Safety Data

• Hazardous Substances Data: 53612-87-6(Hazardous Substances Data)

Upstream product

• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 13433-00-6 diethyl aminomalonate hydrochloride 
• 104-21-2 p-methoxybenzyl acetate 
• 270921-39-6 (4-methoxyphenyl)methyl methyl carbonate 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 7635-29-2 O-methyl tyrosine 
• 856571-30-7 2-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}-3-(4-methoxyphenyl)propionic acid ethyl ester 
• 856571-11-4 2-(2-aminobenzoylamino)-3-(4-methoxyphenyl)propionic acid ethyl ester 
• 67423-44-3 2-amino-3-(4-methoxyphenyl)propionic acid hydrochloride 
• 556-02-5 ?Tyr 

Relevant articles and documents

Room-Temperature Benzylic Alkylation of Benzylic Carbonates: Improvement of Palladium Catalyst and Mechanistic Study

The palladium catalyst for the nucleophilic substitution of benzyl carbonates was improved by using 1,1′-bis(diisopropylphosphino)ferrocene (DiPrPF) as the ligand. The [Pd(η3-C3H5)(cod)]BF4-DiPrPF catalyst allows the benzylic substitution with soft carbanions to proceed even at 30 °C, affording the desired products in high yields (up to 99% yield). Thermally unstable pyridylmethyl esters are employable as the electrophilic substrates for the benzylic alkylation with the improved catalyst. Furthermore, we investigated the mechanism of the catalytic benzylic alkylation by means of DiPrPF ligand. The palladium(0) complex bearing DiPrPF activates the benzylic C-O bond to form the (benzyl)palladium(II) intermediate at room temperature. The coordination mode of the benzyl ligand would be equilibrium between the η1- and η3-manner. The nucleophile would preferentially react with the η3-benzyl ligand to give the desired product.

Use of acetate as a leaving group in palladium-catalyzed nucleophilic substitution of benzylic esters

The palladium complex prepared in situ from [Pd(η3-C3H5)(cod)]BF4 and bidentate phosphine DPPF was a good catalyst for the nucleophilic substitution of benzyl acetate. Significant acceleration of the palladium-catalyzed substitution was observed when an alcohol was employed as a reaction solvent. The palladium catalyst was effective for the benzylation of various stabilized carbanions, amines, and benzenesulfinate with benzylic acetates.

Palladium-catalyzed benzylation of active methine compounds without additional base: Remarkable effect of 1,5-cyclooctadiene

(Chemical Equation Presented) The palladium complex prepared from DPPF and Cp(η3-C3H5)Pd is an effective catalyst for the alkylation of active methine compounds with benzylic carbonates under neutral conditions. The additi