139983-29-2

Upstream product

• 591-50-4 iodobenzene 
• 147-85-3 L-proline 
• 108-86-1 bromobenzene 
• 67-63-0 isopropyl alcohol 
• 584-08-7 potassium carbonate 
• 146500-37-0 N-phenyl-L-proline methyl ester 
• 98-80-6 phenylboronic acid 

Downstream Products

• 146500-37-0 N-phenyl-L-proline methyl ester 
• 951328-86-2 (S)-tert-butyl methylthio-N-(1-phenylpyrrolidine-5-carbonyl)carbonoimidoylcarbamate 
• 1383548-66-0 ingenol-5,20-acetonide-3-((2S)-1-phenylpyrrolidine-2-carboxylate) 
• 18133-14-7 2-(hydroxymethyl)-N-phenylpyrrolidine 
• 896462-48-9 (S)-2-(benzyloxymethyl)-1-(2-bromophenyl)pyrrolidine 
• 896462-37-6 (S)-(1-(2-bromophenyl)pyrrolidin-2-yl)methanol 
• 896462-45-6 (S)-1-(2-bromophenyl)-2-(methoxymethyl)pyrrolidine 
• 896462-34-3 ((S)-1-phenylpyrrolidin-2-yl)methanol 

Relevant academic research and scientific papers

Synthesis of chiral N-aryl-α-amino acids by Pd-Cu catalyzed couplings of chiral α-amino acids with aryl halides

A concise synthesis of chiral N-aryl-α-amino acids, the common core structures for several biologically important molecules, by Pd-Cu catalyzed coupling of L- or D-α-amino acids and aryl halides, is described. Copyright (C) 1996 Published by Elsevier Scie

Bcl-2 INHIBITORS

Disclosed herein is a compound of Formula (I) for inhibiting Bcl-2 and treating disease associated with undesirable bcl-2 activity (Bcl-2 related diseases), a method of using the compounds disclosed herein for treating dysregulated apoptotic diseases including cancers and treating autoimmune disease, and a pharmaceutical composition comprising the same.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF

Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

Copper-catalyzed: N -(hetero)arylation of amino acids in water

An environmentally benign, mild, cost-effective and gram-scalable copper-catalyzed method for the N-(hetero)arylation of zwitterionic natural and unnatural amino acids using 2-isobutyrylcyclohexanone as a β-diketone ligand and aryl bromides as coupling partners in water for 50 min at 90 °C under microwave irradiation is reported. Electronically and sterically diverse aryl coupling partners were inserted efficiently, including challenging heteroaryl electrophilic partners in high yields without affecting the enantiopurity of the product.

Macrocyclic prolinyl acyl guanidines as inhibitors of β-secretase (BACE)

The synthesis, evaluation, and structure-activity relationships of a class of acyl guanidines which inhibit the BACE-1 enzyme are presented. The prolinyl acyl guanidine chemotype (7c), unlike compounds of the parent isothiazole chemotype (1), yielded compounds with good agreement between their enzymatic and cellular potency as well as a reduced susceptibility to P-gp efflux. Further improvements in potency and P-gp ratio were realized via a macrocyclization strategy. The in vivo profile in wild-type mice and P-gp effects for the macrocyclic analog 21c is presented.

Ligand-free copper(i) oxide nanoparticle-catalysed amination of aryl halides in ionic liquids

In the following, we present a simple and feasible methodology for a C-N coupling reaction using nanoscale Cu2O catalysts incorporated in n-Bu4POAc ionic liquid media. It is shown that a wide range of amines and aryl halides can be coupled selectively in high yields, without the use of ligands or additives (bases) and without precautions against water or air. All catalyses can be carried out with a nanoparticle catalyst loading as low as 5 mol%, based on the used precursor.

A mild and catalyst-free aromatization using dihydroxylcyclohexanone derivatives as phenyl sources: A new approach to anilines

A new and efficient protocol for the preparation of N-substituted anilines via an aromatization reaction was developed. 3,5-Dihydroxylcyclohexanone derivatives were used as the sources of the phenyl group and reacted smoothly with primary or secondary amines under mild conditions in the absence of metal catalyst and strong base. A variety of N-substituted anilines were prepared by this method with excellent yields up to 99%. The results indicate that this reaction begins with a nucleophilic addition.

Imidazole-coordinated monodentate NHC-Pd(II) complex derived from proline and its application to the coupling reaction of arylboronic acids with carboxylic acid anhydrides in water at room temperature

Cleavage of a C-N bond of imidazolium salt derived from N-phenyl-substituted proline was observed in this laboratory. A novel imidazole-coordinated monodentate NHC-Pd(II) complex 5 was obtained as the sole product in good yield in the reaction of imidazolium salt 4 with Pd(OAc) 2 in refluxing THF. The structure of complex 5 was determined unambiguously by an X-ray diffraction. The complex was found to be a good catalyst in the cross-coupling reaction of arylboronic acids with carboxylic acid anhydrides in water at room temperature. Copyright

Use of diphenyliodonium bromide in the synthesis of some N-phenyl-amino acids

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 C-N coupling reactions of aryl halides with α-amino acids under focused microwave irradiation

We have developed an efficient method for the preparation of enantiopure N-aryl-α-amino acids via copper-catalyzed N-arylation of α-amino acids and aryl halides under microwave irradiation. This protocol only needs less than 30 min to obtain the products,