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Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-Carbamoyl-2-methylpropionic acid is used as an intermediate in the biosynthesis of certain molecules for pharmaceutical applications. Its role in the production of peptides and other organic compounds makes it a valuable component in the development of new drugs and therapeutic agents.
Used in Biotechnology Industry:
In the biotechnology sector, (S)-3-Carbamoyl-2-methylpropionic acid serves as a key intermediate in the synthesis of biologically active molecules. Its potential applications in this industry include the creation of novel drugs and therapeutic agents that can address various health concerns and medical conditions.

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 academic research and scientific papers

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

DiPAMP's big brother "i-Pr-SMS-Phos" exhibits exceptional features enhancing rhodium(I)-catalyzed hydrogenation of olefins

Switching Knowles DiPAMP's {DiPAMP = l,2-bis[(o-anisyl)(phenyl)phosphino] ethane} MeO groups with i-PrO ones led to the iPr-SMS-Phos {i-Pr-SMS-Phos = l,2-bis[(o-isopropoxyphenyl)(phenyl)phosphino]ethane} ligand which displayed a boosted catalyst activity coupled with an enhanced enantioselectivity in the rhodium(I)catalyzed hydrogenation of a wide-range of representative olefinic substrates (dehydro-a-amido acids, itaconates, acrylates, enamides, enol acetates, α,α-diarylethylenes, etc). The rhodium(I)-(i-PrSMS-Phos) catalytic profile was investigated revealing its structural attributes and robustness, and in contrast to the usual trend, 31P NMR analysis revealed that its methyl (Z)-α-acetamidocinnamate (MAC) adduct consisted of a reversed diastereomeric ratio of 1.4:1 in favour of the most reactive diastereomer.

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.

Efficient preparation of optically active (S)-(-)-3-methyl-γ-butyrolactone by catalytic asymmetric hydrogenation using chiral N-substituted pyrrolidinebisphosphine rhodium complexes

(S)-(-)-2-Methyl succinamic acid, which is a good precursor of (S)-(-)-3-methyl-γ-butyrolactone, can be prepared by homogeneous asymmetric hydrogenation of 2-methylene succinamic acid catalyzed by (2S,4S)-N-substituted-4-(diphenylphosphino)-2-[(diphenylphosphino)-meth yl]pyrrolidine-rhodium complexes. Various N-substituted pyrrolidine-bisphosphines were synthesized to find the optimum ligand for this purpose and to compare the effects of the N-substituents.