69632-50-4

Basic information

• Product Name: Benzeneacetic acid, a-[(3,5-dinitrobenzoyl)amino]-, methyl ester, (R)-
• CAS NO: 69632-50-4
• Molecular Formula: C16H13N3O7
• Molecular Weight: 359.295
• Mol File: 69632-50-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzeneacetic acid, a-[(3,5-dinitrobenzoyl)amino]-, methyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-[(3,5-dinitrobenzoyl)amino]-, methyl ester, (R)-(69632-50-4)
• EPA Substance Registry System: Benzeneacetic acid, a-[(3,5-dinitrobenzoyl)amino]-, methyl ester, (R)-(69632-50-4)

Safety Data

• Hazardous Substances Data: 69632-50-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 74927-72-3 (R)-(-)-N-(3,5-dinitrobenzoyl)-α-phenylglycine 

Relevant articles and documents

Enantioselective hydrolysis of N-acylated α-amino esters at a biphasic interface: Tandem reaction kinetic resolution using a chiral complexing agent

equation presented Highly enantioselective hydrolytic kinetic resolutions of esters derived from N-acylated α-amino acids proceed rapidly at hydrocarbon/water interfaces in the presence of a proline-derived chiral selector. When performed in tandem with an enantioselective biphasic esterification reaction, esters of 100% enantiomeric excess are obtained.

Synthesis of (R)-(-) and (S)-(+)-3-(1-pyrrolyl)propyl- N-(3,5- dinitrobenzoyl)-α-phenylglycinate and derivatives. A suitable chiral polymeric phase precursor

A synthetic route to obtain (R)-(-) (1), (S)-(+)-3-(1-pyrrolyl)propyl-N- (3,5-dinitrobenzoyl)-α-phenylglycinate (2) and derivatives is described. In a first step, pyrrole derivatives were prepared using the Clauson-Kaas method. The esterification, second step, was performed using basic conditions due to sensitivity of the pyrrole group toward acidic conditions. A tautomeric equilibrium involving the stereogenic center induces the product epimerization. The substitution of DMAP and Et3N by a highly hindered base, proton-sponge, furnished the final products without racemization. The ee of 1, 2 and of the corresponding methyl esters (3 and 4) were determined by 1H NMR analysis in the presence of optically active Eu(tfc)3. Epimerization was not observed in the preparation of the carboxylate salts (5-8).