74518-47-1

Upstream product

• 67-56-1 methanol 
• 882-36-0 N-benzyl-3-oxobutanamide 
• 100-46-9 benzylamine 
• 5704-66-5 pyruvoyl chloride 
• 74-88-4 methyl iodide 
• 5781-53-3 monomethyl oxalyl chloride 
• 4916-26-1 (Z)-<1,2-bis(methoxycarbonyl)vinyl>aminotoluene 
• 74518-34-6 1,3-Dibenzyl-2-oxo-2-phenoxy-2λ⁵-[1,3,2]diazaphospholidine-4,5-dione 
• 4257-83-4 benzyl 2,2,2-trichloroacetamide 

Downstream Products

• 96042-95-4 2-(Benzylaminooxalyl-amino)-3-phenyl-propionic acid methyl ester 
• 96094-76-7 (S)-2-(Benzylaminooxalyl-amino)-3-phenyl-propionic acid methyl ester 
• 321860-04-2 N-benzyl-N-(2-oxo-ethyl)-oxalamic acid methyl ester 
• 96042-96-5 2-(2-(benzylamino)-2-oxoacetamido)acetic acid 
• 3173-56-6 benzyl isothiocyanate 
• 321860-07-5 1-benzyl-4-cyclopropyl-piperazine-2,3-dione 
• 321860-08-6 1-benzyl-4-isopropyl-piperazine-2,3-dione 

Relevant academic research and scientific papers

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.

Oxalohydrazide Ligands for Copper-Catalyzed C?O Coupling Reactions with High Turnover Numbers

Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C?O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.

Copper-Catalysed (Diacetoxyiodo)benzene-Promoted Aerobic Esterification Reaction: Synthesis of Oxamates from Acetoacetamides

A copper-catalysed (diacetoxyiodo)benzene-promoted aerobic esterification reaction of acetoacetamides was developed for the synthesis of oxamates, which are useful precursors in synthetic organic chemistry. This practical and mild synthetic approach proceeded at 25 °C under open-air conditions and afforded methyl 2-oxo-2-(phenylamino)acetates in good to excellent yields combined with C?C σ-bond cleavage and formal oxidative C?H bond functionalization. A mechanism is proposed. (Figure presented.).

2-Oxoglutarate analogue inhibitors of prolyl hydroxylase domain 2

Analogues of the 2-oxoglutarate cosubstrate of the human oxygen sensing enzyme prolyl hydroxylase domain 2 (PHD2) with variations in the potential iron-chelating group were screened as inhibitors and for binding (using non-denaturing electrospray ionization mass spectrometry) to PHD2.

First-in-class pan caspase inhibitor developed for the treatment of liver disease

A series of oxamyl dipeptides were optimized for pan caspase inhibition, anti-apoptotic cellular activity and in vivo efficacy. This structure-activity relationship study focused on the P4 oxamides and warhead moieties. Primarily on the basis of in vitro data, inhibitors were selected for study in a murine model of α-Fas-induced liver injury. IDN-6556 (1) was further profiled in additional in vivo models and pharmacokinetic studies. This first-in-class caspase inhibitor is now the subject of two Phase II clinical trials, evaluating its safety and efficacy for use in liver disease.

Oxamyl dipeptide caspase inhibitors developed for the treatment of stroke

Structural modifications were made to a previously described acyl dipeptide caspase inhibitor, leading to the oxamyl dipeptide series. Subsequent SAR studies directed toward the warhead, P2, and P4 regions of this novel peptidomimetic are described herein.

Efficient synthesis of unsymmetrical 1,4-disubstituted-2,3-diketopiperazines via tandem reductive amination-cyclization

Herein we report the efficient syntheses of 1,4-disubstituted-2,3-diketopiperazines and 1,4,5-trisubstituted-2,3-diketopiperazines, which feature a tandem reductive amination and acylation. Aliphatic and aromatic primary amines serve as viable nucleophiles under the mild reaction conditions. (C) 2000 Elsevier Science Ltd.

Reactivity of Carbamoyl Radicals. A New, General, Convenient Free-Radical Synthesis of Isocyanates from Monoamides of Oxalic Acid

A new, general, simple synthesis of isocyanates was developed by oxidation of monoamides of oxalix acid with peroxydisulfate catalyzed by Ag and Cu salts.The reaction was carried out in a two-phase system (water and an organic solvent), and it is suitable also for practical applications, due to the simple experimental conditions and the inexpensive as well as nontoxic reagents.The first example of homolytic intramolecular aromatic carbamoylation is also reported.

Photoinduced Alcoholysis of Trihaloacetyl Group

Photolysis of trichloroacetamide in nondegassed methanol gave methyl oxanilate (13-44percent), along with carbamate (3-20percent) and amine (4-12percent).Similar irradiation of other trichloroacetylderivatives of aliphatic ketone, aldehyde, and acetate afforded only radical product.The results are interpreted in terms of the mechanism involving electron transfer of the radical pair.