67412-96-8

Usage

Uses

Used in Pharmaceutical Industry:
R-Alpha-Amino-4-Methoxybenzene Acetamide is used as a key building block in the synthesis of various pharmaceutical compounds for its analgesic and anti-inflammatory properties. It plays a crucial role in the development of pain relief medications, offering effective solutions for managing pain and inflammation.
Used in Chemical Industry:
R-Alpha-Amino-4-Methoxybenzene Acetamide is used as a raw material in the production of dyes, pigments, and other organic compounds. Its versatility and chemical properties make it a valuable component in the creation of a wide range of chemical products, contributing to the diversity and functionality of the chemical industry.

InChI:InChI=1/C9H12N2O2/c1-13-7-4-2-6(3-5-7)8(10)9(11)12/h2-5,8H,10H2,1H3,(H2,11,12)/t8-/m1/s1

Upstream product

• 76986-15-7 2-amino-2-(4-methoxyphenyl)acetamide 
• 42456-26-8 2-amino-2-(4-methoxyphenyl)acetonitrile 
• 60827-77-2 (R)-(N-benzyloxycarbonyl)-p-methoxyphenylglycine 

Downstream Products

• 1000307-35-6 2-(R)-(4-methoxyphenyl)-2-[2-(4-methoxyphenyl)acetylamino]-acetamide 

Relevant academic research and scientific papers

BMS-201620: A selective beta 3 agonist

A series of N-(4-hydroxy-3-methylsulfonanilidoethanol)arylglycinamides were prepared and evaluated for their human β3 adrenergic receptor agonist activity. SAR studies led to the identification of BMS-201620 (39), a potent β3 full agonist (Ki=93nM, 93% activation). Based on its favorable safety profile, BMS-201620 was chosen for clinical evaluation.

Practical and convenient enzymatic synthesis of enantiopure α-amino acids and amides

Catalyzed by the nitrile hydratase and the amidease in Rhodococcus sp. AJ270 cells under very mild conditions, a number of α-aryl- and α-alkyl-substituted DL-glycine nitriles 1 rapidly underwent a highly enantioselective hydrolysis to afford D-(-)-α-amino acid amides 2 and L-(+)-α-amino acids 3 in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of a high L-enantioselective amidase and a low enantioselective nitrile hydratase. The influence of the substrates on both reaction efficiency and enantioselectivity was also discussed in terms of steric and electronic effects. Coupled with chemical hydrolysis of D-(-)-α-phenylglycine amide, biotransformation of DL-phenylglycine nitrile was applied in practical scale to produce both D- and L-phenylglycines in high optical purity.

Highly efficient and enantioselective synthesis of L-arylglycines and D-arylglycine amides from biotransformations of nitriles

Under very mild conditions, the Rhodococcus sp. AJ270-catalysed biotransformation of arylglycine nitriles 1, prepared easily from the reaction of substituted benzaldehydes, ammonium chloride and potassium cyanide, proceeded efficiently to produce optically active D-arylglycine amides 2 and L-arylglycines 3 in excellent yields with enantiomeric excesses higher than 99%.

Quantitative Approaches to Optical Resolution. Part 1. Resolution of DL-Phenylglycine Derivatives with (+)-Tartaric Acid

The results of 23 cases of resolution of DL-phenyldlycine derivatives (I) with (+)-tartaric acid in various solvents are investigated, using correlation analysis, as a function of the introduced racemic compounds and the solvent used.A procedure, combining three quantitative structure-activity relationship methods, i.e.Golender and Rozenblit's logico-structural approach with the Free-Wilson and Hansch analyses, resulted in statistically significant relationships.It is suggested that the solvent may exert two kinds of influence: (1) the higher the solvent polarity, the more likely the L-(I) salt to crystallise; (2) alcoholic mixtures, although being highly polar, favour the precipitation of the D-(I) salt rather than that of the L-(I) salt, probably due to a selective interaction with the diastereomers.As to the racemic compound, the relationships obtained are in accord with literature statements that resolution proceeds by a multiple interaction mechanism.