5428-44-4Relevant academic research and scientific papers
Room temperature N-arylation of amino acids and peptides using copper(i) and β-diketone
Sharma, Krishna K.,Sharma, Swagat,Kudwal, Anurag,Jain, Rahul
supporting information, p. 4637 - 4641 (2015/04/27)
A mild and efficient method for the N-arylation of zwitterionic amino acids, amino acid esters and peptides is described. The procedure provides the first room temperature synthesis of N-arylated amino acids and peptides using CuI as a catalyst, diketone as a ligand, and aryl iodides as coupling partners. The method is equally applicable for using relatively inexpensive aryl bromides as coupling partners at 80 °C. Using this procedure, electronically and sterically diverse aryl halides, containing reactive functional groups were efficiently coupled in good to excellent yields.
Use of diphenyliodonium bromide in the synthesis of some N-phenyl-amino acids
McKerrow, Jason D.,Al-Rawi, Jasim M. A.,Brooks, Peter
experimental part, p. 1161 - 1179 (2010/04/28)
The N-phenyl methyl esters 4 of glycine, alanine, valine, leucine, isoleucine, phenylalanine, methionine, proline, serine, threonine, tyrosine, aspartic acid, and glutamic acid have been synthesized in good to excellent yields using diphenyliodonium bromide, AgNO3, and a catalytic amount of CuBr starting from the relevant amino acid ester. The chiral integrity of the amino acids 5 was maintained during these reactions, which were confirmed by the synthesis of dipeptide for each N-phenyl amino acid. The structures of the new compounds were confirmed by the analysis of their IR, 1H, and 13C NMR spectra in addition to CHN microanalysis or high-resolution mass spectrometry for the new N-phenyl amino acids 5 and the esters 4.
Copper-catalyzed aryl amination in aqueous media with 2- dimethylaminoethanol ligand
Lu, Zhikuan,Twieg, Robert J.
, p. 2997 - 3001 (2007/10/03)
Copper-catalyzed amination of aryl bromides and iodides under mild conditions has been developed with 2-dimethylaminoethanol as ligand and water as solvent. A variety of hydrophilic and hydrophobic aryl halide substrates have been aminated in good yield with a variety of amino acids, amino alcohols and peptides. This method has successfully N-arylated some hydrophilic amino compounds not available by other methods.
2,5-diamino-1,4-dioxane derivatives and process for production thereof
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, (2008/06/13)
Dioxane derivatives are disclosed which are represented by the formula (I): STR1 wherein, R stands for a hydrogen atom or an aliphatic residue having 1 to 10 carbon atoms; R1 and R2 stand for a hydrogen atom or a hydrocarbon residue having 1 to 10 carbon atoms, respectively; and R, R1 and R2 which exist plurally may be the same or different, respectively. Such dioxane derivatives (I) are produced by reacting a glycolaldehyde represented by the formula (II) STR2 with an amine represented by the formula (III) wherein R, R1 and R2 are as defined above. The dioxane derivatives (I) are useful for production of serine derivatives as well as utilized for separation and purification of glycolaldehydes (II).
Process for preparing α-L-aspartyl-L-phenylalanine methyl ester
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, (2008/06/13)
A process for preparing α-L-aspartyl-L-phenylalanine methyl ester: STR1 in which: (a) the compound methyl N(α-L-aspartyl)α-aminocinnamate, protected at the nitrogen, of formula: STR2 where R is a protector group at the nitrogen, is subjected to hydrogenation at the olefin bond by means of gaseous hydrogen in the presence of a hydrogenation catalyst, to give the compound of formula: STR3 where R has the aforesaid meaning, in the form of a mixture of α-L-aspartyl-L-phenylalanine methyl ester protected at the nitrogen, and α-L-aspartyl-D-phenylalanine methyl ester protected at the nitrogen; (b) the protector group is removed from the α-L-aspartyl-L-phenylalanine and α-L-aspartyl-D-phenylalanine methyl esters protected at the nitrogen; (c) the α-L-aspartyl-L-phenylalanine methyl ester is separated and recovered from the deprotection reaction product.
