1126476-86-5

Upstream product

• 1126476-75-2 (S)-tert-butyl-5-((S)-1-methoxy-3-methyl-1-oxobutan-2-ylcarbamoyl)-3-oxo-2-phenylpyrazolidine-1-carboxylate 
• 1222313-86-1 (S)-1-phenylethylammonium (S)-5-oxo-1-phenylpyrazolidine-3-carboxylate 
• 100-63-0 phenylhydrazine 

Downstream Products

• 1222313-88-3 (S)-methyl 5-oxo-1-phenylpyrazolidine-3-carboxylate 

Relevant academic research and scientific papers

Biocatalytic Asymmetric Synthesis of N-Aryl-Functionalized Amino Acids and Substituted Pyrazolidinones

N-arylated α-amino acids and pyrazolidin-3-ones are widely being used as chiral building blocks for pharmaceuticals and agrochemicals. Here we report a biocatalytic route for the asymmetric synthesis of various N-arylated aspartic acids applying ethylenediamine-N,N′-disuccinic acid lyase (EDDS lyase) as a biocatalyst. This enzyme shows a broad substrate scope, enabling the addition of a variety of arylamines to fumarate with high conversions, yielding the corresponding N-arylated aspartic acids in good isolated yields and with high enantiomeric excess (ee > 99%). Furthermore, we developed a chemoenzymatic method toward the synthetically challenging chiral 2-aryl-5-carboxylpyrazolidin-3-ones, using arylhydrazines as bis-nucleophilic donors in the EDDS lyase catalyzed hydroamination of fumarate followed by an acid-catalyzed intramolecular amidation, achieving good overall yields and high optical purity (ee > 99%). In addition, we successfully combined the EDDS lyase catalyzed hydroamination and acid-catalyzed cyclization steps in one pot, thus providing a simple chemoenzymatic cascade route for synthesis of enantiomerically pure pyrazolidin-3-ones. Hence, these biocatalytic methods provide convenient alternative routes to important chiral N-arylated aspartic acids and difficult 2-aryl-5-carboxylpyrazolidin-3-ones.

Resolution of 5-oxo-1-phenylpyrazolidine-3-carboxylic acid and synthesis of novel enantiopure amide derivatives

The synthesis is reported of (±)-5-oxo-1-phenylpyrazolidine-3- carboxylic acid, (±)-3, via nucleophilic addition of phenylhydrazine to dimethyl maleate, followed by cyclization of the resulting hydrazine-diester. The resolution of (±)-3 was achieved via diastereomeric salts employing (R)- and (S)-a-methylbenzylamine as resolving agent. Preferential crystallization of the like (R,R)- and (S,S)- salts allowed the isolation of the desired enantiomerically pure (R)- and (S)- target compounds in up to 87-89 % of the theoretical yield. An X-ray structure of the (S,S)- salt allowed secure assignment of its relative configuration, and thus unequivocal assignment of the absolute configuration in the enantiomeric heterocycles.

Optical resolution of 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid as a new organocatalyst for organic reactions

Optical resolution of racemic 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid 2 with L-amino acid methyl ester via the diastereomers formation was investigated. Treatment of racemic 5-oxo-1-phenylpyrazolidine-3-carboxylic acid 2 with L-valine methyl ester g