63526-79-4

Upstream product

• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 43041-59-4 methyl (S)-(-)-2-isocyano-3-phenylpropionate 
• 2311-21-9 N-formyl-L-phenylalanine-methylester 
• 15028-44-1 DL-phenylalanine methyl ester 
• 150-30-1 Phenylalanine 

Downstream Products

• 112681-17-1 (2R,1'S)-2-isocyano-3-phenyl-N-(1'-phenylethyl)propionamide 
• 112681-16-0 (S)-2-isocyano-3-phenyl-N-((S)-1-phenyl-ethyl)-propionamide 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 57519-78-5 methyl 2-cyano-4-phenylpropanoate 

Relevant academic research and scientific papers

Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides

The synthesis of a novel category of pseudo-peptides via intramolecular Ugi reaction of levulinic acid (4-oxopentanoic acid), aromatic and aliphatic amines, and amino acid-based isocyanides is reported. Levulinic acid was applied as a bifunctional substrate containing both carbonyl and acid moieties suitable for the Ugi reaction. This article provides a facile and convenient one-pot procedure for the synthesis of peptide-like heterocyclic molecules containing 2-pyrrolidone (γ-lactam), amide and ester functional groups with good to excellent yields.

Chiral trans-carboxylic trifluoromethyl 2-imidazolines by a Ag2O-catalyzed Mannich-type reaction

Trifluoromethyl aldimines derived from α-amino esters have proven to be very good starting materials to obtain the title compounds. A Ag2O-catalyzed Mannich-type/cyclization cascade reaction starting from suitable α-isocyano acetates leads to e

Isocyanides as influenza A virus subtype H5N1 wild-type M2 channel inhibitors

Basic bulky amines such as amantadine are well-characterized M2 channel blockers, useful for treating influenza. Herein we report our surprising findings that charge-neutral, bulky isocyanides exhibit activities similar to - or even higher than - that of amantadine. We also demonstrate that these isocyanides have potent growth inhibitory activity against the H5N1 virus. The -NH2 to -N≡C group replacement within current anti-influenza drugs was found to give compounds with high activities at low-micromolar concentrations. For example, a tenfold improvement in potency was observed for 1-isocyanoadamantane (27), with an EC50 value of 0.487 μm against amantadine-sensitive H5N1 virus as determined by both MTT and plaque-reduction assays, without showing cytotoxicity. Furthermore, the isocyanide analogues synthesized in this study did not inhibit the V27A or S31N mutant M2 ion channels, according to electrophysiology experiments, and did not exhibit activity against amantadine-resistant virus strains. Charge-neutral bulky isocyanides were found to exhibit antiviral activities similar to - or even higher than - that of amantadine. Moreover, we demonstrated that these isocyanides have potent growth inhibitory activity against the wild-type H5N1 virus. The NH2 to N≡C group replacement within current anti-influenza drugs was found to result in compounds with low-micromolar activities.

Triple role of phenylselenonyl group enabled a one-pot synthesis of 1,3-oxazinan-2-ones from α-isocyanoacetates, phenyl vinyl selenones, and water

Reaction of α-substituted α-isocyanoacetates with phenyl vinyl selenones in the presence of a catalytic amount of base (DBU or Et3N, 0.05-0.1 equiv) followed by addition of p-toluenesulfonic acid (PTSA, 0.1-0.2 equiv) afforded 4,4,5-trisubstituted 1,3-oxazinan-2-ones in good to excellent yields. Enantiomerically enriched heterocycles can also be prepared using a Cinchona alkaloid-derived bifunctional organocatalyst for the Michael addition step. The phenylselenonyl group served as an activator for the Michael addition, a leaving group and a latent oxidant in this integrated reaction sequence.

A cation-directed two-component cascade approach to enantioenriched pyrroloindolines

A cascade approach to complex pyrroloindolines bearing all-carbon quaternary stereocentres has been developed. This two-component process uses a chiral ammonium salt to control diastereo- and enantioselectivity in the addition of isocyanides to functionalized alkenes to afford pyrroloindolines with up to three stereocentres. A mechanistic proposal involving intramolecular hydrogen bond activation of the isocyanide is described.

Copper-catalyzed enantioselective intramolecular N -arylation, an efficient method for kinetic resolutions

For the first time, copper-catalyzed intramolecular N-arylation was successfully applied to the kinetic resolution strategy. Under the catalysis of CuI-BINOL derived ligands, the kinetic resolution of rac-2-amino-3-(2-iodoaryl) propionates and rac-2-amino-4-(2-iodoaryl)butanoates afforded chiral intramolecular coupling products and recovered the starting materials in high enantioselectivity (s factors up to 245).

On the preparation of enantiomerically pure isonitriles from amino acid esters and peptides

An improved method for the synthesis of enantiomerically pure isonitriles from amino acid esters and dipeptides is described.

Application of isocyanides derived from α-amino acids as substrates for the Ugi reaction

A systematic study on the influence of Lewis acid, solvent, and temperature on the stereochemical course of the Ugi reaction was performed to find conditions in which the isocyanides derived from enantiopure α-amino acids do not racemize. After a series o

A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines

(Chemical Equation Presented) A multicomponent reaction between α-acidic isonitriles, primary amines, and carbonyl compounds was studied using 14 different solvents. Depending on the isocyanide that was used, optimal yields for the three-component synthesis of 2H-2-imidazolines were observed in different solvents. The solvents could be used as purchased, and in situ preformation of the imine was not required. By selecting the appropriate solvent, it was possible to considerably expand the range of compatible isocyanides toward less α-acidic isocyanides. Further process simplification was achieved by performing the reaction at higher concentrations and avoiding purification by column chromatography, resulting in a fast, easy to perform, and resource-efficient protocol for this three-component reaction.