72342-65-5

Basic information

• Product Name: (S)-3-Carbamoyl-2-methylpropionic acid
• Synonyms: (S)-3-Carbamoyl-2-methylpropionic acid;4-Amino-2-methyl-4-oxo-(2S)-butanoic acid
• CAS NO: 72342-65-5
• Molecular Formula: C₅H₉NO₃
• Molecular Weight: 131.12986
• Mol File: 72342-65-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-Carbamoyl-2-methylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Carbamoyl-2-methylpropionic acid(72342-65-5)
• EPA Substance Registry System: (S)-3-Carbamoyl-2-methylpropionic acid(72342-65-5)

Safety Data

• Hazardous Substances Data: 72342-65-5(Hazardous Substances Data)

Usage

General Description

(S)-3-Carbamoyl-2-methylpropionic acid is a chemical compound with the molecular formula C6H11NO3. It is an organic compound that contains a carboxylic acid functional group and a carbamoyl group. (S)-3-Carbamoyl-2-methylpropionic acid is also known as N-carbamoyl-DL-alanine and is used as an intermediate in the biosynthesis of certain molecules in living organisms. It is also used in the production of peptides and other organic compounds. This chemical has potential applications in the pharmaceutical and biotechnology industries for the development of new drugs and therapeutic agents. Overall, (S)-3-Carbamoyl-2-methylpropionic acid is a versatile compound with various potential uses in different fields.

Upstream product

• 54468-53-0 4-amino-2-methylene-4-oxo-butanoic acid 
• 357-57-3 brucine 

Downstream Products

• 64190-48-3 (S)-3-methyl-4-butanolide 
• 144-90-1 (S)-(+)-β²-homoalanine 

Relevant articles and documents

Modular P-OP ligands in rhodium-mediated asymmetric hydrogenation: A comparative catalysis study

Highly efficient and enantioselective hydrogenation reactions for α-(acylamino)acrylates, itaconic acid derivatives and analogues, α-substituted enol ester derivatives, and α-arylenamides (25 substrates) catalyzed by chiral cationic rhodium complexes of a set of P-OP ligands have been developed. The catalytic systems derived from these P-OP ligands provided a straightforward access to enantiomerically enriched α-amino acid, carboxylic acid, amine, and alcohol derivatives that are valuable chiral building blocks. Excellent efficiencies (full conversion in all cases) and extremely high enantiomeric excesses (94-99% ee) were achieved for a wide range of α-substituted enol ester derivatives, regardless of the substitution pattern. The R-oxy group of the ligand (methoxy or triphenylmethoxy) strongly influences the enantioselectivity and catalytic activity. Greater steric bulk around the metal centre correlated to greater (or similar) enantioselectivity, but also to slower hydrogenation. Furthermore, the hydrogenation rates observed with the four model substrates follow the same trend, independently of the R-oxy group of the ligand: methyl 2-acetamidoacrylate>dimethyl itaconate>1-phenylvinyl acetate>N-(1- phenylvinyl)acetamide. A substrate-to-catalyst ratio (S/C) of up to 10,000:1 was sufficient for total hydrogenation of a model substrate of intermediate reactivity (dimethyl itaconate), and did not imply any loss in conversion or enantioselectivity. Copyright

Highly efficient asymmetric hydrogenation of 2-methylenesuccinamic acid using a Rh-DuPHOS catalyst

An extremely efficient route to highly enantiomerically enriched 2-methylsuccinamic acid via asymmetric hydrogenation has been developed. By using [(S,S)-Et-DuPHOS Rh COD]BF4 as the precatalyst under a set of broadly optimised process parameters, (R)-2-methylsuccinamic acid was obtained in 96% ee at a substrate-to-catalyst ratio (S/C) of 100000 (average turnover frequency ～13000 h-1). The exclusion of chloride-containing contaminants in the substrate was found to be crucial in obtaining exceptionally low catalyst loadings. This material could be upgraded with a single-crystal digestion to yield (R)-2.methylsuccinamic acid in >99.5% ee containing less than 1 ppm rhodium.