60272-64-2

Upstream product

• 17966-68-6 N-benzoylaspartic acid 
• 2177-62-0 β-methyl L-aspartate 
• 98-88-4 benzoyl chloride 
• 39741-26-9 N-benzoyl-L-aspartic acid β-methyl ester 
• 108541-05-5 N-benzoylaspartic acid β-methyl ester 

Downstream Products

• 60272-69-7 (4-allyl-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-acetic acid methyl ester 
• 71953-20-3 [5-oxo-4-(3-oxo-3-phenyl-trans-propenyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid methyl ester 
• 1562416-43-6 C₁₃H₁₅NO₅ 
• 86555-45-5 (2S)-N-benzoyl-L-aspartic acid dimethyl ester 
• 71953-38-3 3,6-Dioxo-6-phenylhexansaeuremethylester 
• 134308-22-8 4-benzoylamino-4-carboxy-γ-butyrolactone 
• 97640-33-0 4-benzoylamino-4-carboxy-γ-butyrolactone 
• 97640-32-9 4-benzoylamino-4-carboxy-γ-butyrolactone 
• 97640-31-8 N-benzoyl-α-hydroxymethylaspartic acid β-methyl ester 
• 65133-31-5 2-phenyl-6H-1,3-oxazin-6-one 
• 62183-17-9 (Z)-methyl 3-(benzamido)acrylate 
• 62183-16-8 methyl (E)-3-benzamidoacrylate 
• 97640-30-7 5-benzoylamino-5-methoxycarbonylmethylene-4-oxo-1,3-dioxane 

Relevant academic research and scientific papers

Dynamic Kinetic Resolution of Azlactones by a Chiral N, N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups

A dynamic kinetic resolution (DKR) of azlactones in the presence of benzoic acid and a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1i having two amide groups at the 3,3′-positions of a binaphthyl unit is developed. The reaction proceeded smoothly with a wide range of azlactones to provide α-amino acid derivatives with good to high enantiomeric ratios (er's). A multigram-scale reaction (2.5 g) for the DKR of azlactone 2d was also demonstrated, and the resulting product was converted to unnatural α-amino acid 6d′.

Peptide-catalyzed conversion of racemic oxazol-5(4 H)-ones into enantiomerically enriched α-amino acid derivatives

We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

α-Hydroxymethylaspartic acid: Synthesis and absolute configuration by X-ray analysis of its derivative (+)-4-benzoylamino-4-carboxy-γ-butyrolactone

(+)-4-Benzoylamino-4-carboxy-γ-butyrolactone was synthesized, and its structure solved by direct methods and refined to R = 0.033.The molecule adopts a skew conformation with a C7-N1-C8-C12 torsion angle of 59.6(2) deg.The lactone ring has an envelope con