105909-91-9Relevant academic research and scientific papers
Preparation method of chiral alpha-amino acid
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Paragraph 0057; 0058; 0059, (2016/10/08)
The invention discloses a preparation method of chiral alpha-amino acid. Initial raw materials comprising aldehyde and N-acryl substituted glycine undergo Erlenmeyer-Plochl cyclization, hydrolysis or alcoholysis, asymmetric catalytic hydrogenation and acid hydrolysis to obtain the chiral alpha-amino acid compound. The method adopting the above synthesis route has the advantages of mild reaction conditions, simple technological operation, safe and stable production, realization of high yield, good chemical purity and good optical purity of the above obtained product, wide application range, and suitableness for industrial production.
Synthesis of new β-amidodehydroaminobutyric acid derivatives and of new tyrosine derivatives using copper catalyzed C-N and C-O coupling reactions
Pereira,Vilaca,Ferreira
, p. 335 - 344 (2013/07/05)
Several β-amidodehydroaminobutyric acid derivatives were prepared from N,C-diprotected β-bromodehydroaminobutyric acids and amides by a copper catalyzed C-N coupling reaction. The best reaction conditions include the use of a catalytic amount of CuI, N,N'-dimethylethylenediamine as ligand and K 2CO3 as base in toluene at 110 C. The stereochemistry of the products was determined using NOE difference experiments and the results obtained are in agreement with an E-stereochemistry. Thus, the stereochemistry is maintained in the case of the E-isomers of β-bromodehydroaminobutyric acid derivatives, but when the Z-isomers were used as substrates the reaction proceeds with inversion of configuration. The use of β- bromodehydrodipeptides as substrates was also tested. It was found that the reaction outcome depend on the stereochemistry of the β- bromodehydrodipeptide and on the nature of the first amino acid residue. The products isolated were the β-amidodehydrodipeptide derivatives and/or the corresponding dihydropyrazines. The same catalytic system (CuI/N,N'- dimethylethylene diamine) was used in the C-O coupling reactions between a tyrosine derivative and aryl bromides. The new O-aryltyrosine derivatives were isolated in moderate to good yields. The photophysical properties of two of these compounds were studied in four solvents of different polarity. The results show that these compounds after deprotection can be used as fluorescence markers.
A mild high yielding synthesis of oxazole-4-carboxylate derivatives
Ferreira, Paula M.T.,Castanheira, Elisabete M.S.,Monteiro, Luís S.,Pereira, Goreti,Vilaa, Helena
scheme or table, p. 8672 - 8680 (2011/01/04)
Several 2,5-disubstituted oxazole-4-carboxylates were prepared in high yields from the methyl esters of N-acyl-β-halodehydroaminobutyric acid derivatives by treatment with a 2% solution of DBU in acetonitrile. The scope of this reaction was investigated a
Addition of molecular fluorine to azlactones: General synthetic method of erythro-β-fluorinated α-amino acids
Kaneko,Chiba,Toyota,Sato
, p. 760 - 765 (2007/10/02)
Reaction of molecular fluorine with unsaturated azlactones derived from appropriate aldehydes (or ketones) and benzoylglycine afforded the difluorinated adducts. The reductive amination reaction of the β-fluorinated α-oxoalkanoic acids obtained from the a
