2642-32-2

Upstream product

• 55740-06-2 phenylmethyl 5-oxo-1,3-oxazolidine-3-carboxylate 
• 100-46-9 benzylamine 
• 105910-06-3 2-methyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 101442-63-1 rac-5-Oxo-2-phenyloxazolidin-3-carbonsaeure-benzylester 
• 100-44-7 benzyl chloride 
• 92234-91-8 Potassium; benzyloxycarbonylamino-acetate 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 4024-42-4 1-(N-benzyloxycarbonyl-glycyloxy)-piperidine 
• 949-90-6 N-(carbobenzyloxy)glycinamide 
• 1738-86-9 Z-Gly-ONp 
• 121611-58-3 Benzyloxycarbonylamino-acetic acid isopropenyl ester 
• 30196-64-6 N-benzyloxycarbonyl-glycine 4-oxo-3,4-dihydro-phthalazin-1-yl ester 
• 30196-63-5 Z-Glycin-N,N'-diphenyl-hydrazid 
• 2899-60-7 Cbz-Gly-ONSuc 

Downstream Products

• 911289-28-6 C₁₅H₁₅N₃O₄*ClH 
• 911289-57-1 C₂₉H₂₇N₃O₄ 
• 39796-52-6 N-benzyl-2-aminoacetamide 

Relevant academic research and scientific papers

Zirconium catalyzed amide formation without water scavenging

A scalable homogeneous metal-catalyzed protocol for direct amidation of carboxylic acids is presented. The use of 2–10?mol% of the commercially available Zr(Cp)2(OTf)2·THF results in high yields of amides at moderate temperature, using an operationally convenient reaction protocol that circumvents the use of water scavenging techniques.

Hafnium-catalyzed direct amide formation at room temperature

Herein, the first example of a metal-catalyzed protocol for direct amidation of nonactivated carboxylic acids at ambient temperature (26 °C) is presented. The mild reaction conditions give rise to high yields of a range of amides in reaction times as short as 90 min, employing a commercial hafnium complex, [Hf(Cp)2Cl2], as catalyst. Amino acids are transformed into their corresponding amides without racemization, and the catalyst displays full selectivity for the amidation of carboxylic acids over esters. Electronic properties of the carboxylic acids were found to have a strong influence on the rate of the amidation reaction, and the need for a balanced amount of molecular sieves was observed to be highly important for optimal reaction outcome.

Chemoselective calcium-catalysed direct amidation of carboxylic esters

Unactivated carboxylic esters and primary amines undergo calcium-catalysed direct amide bond formation in excellent yields under homogeneous conditions in toluene. This green and mild reaction proceeds chemoselectively with esters, whereas related carboxylic acids and amides remain unreactive.

Zirconium-catalyzed direct amide bond formation between carboxylic esters and amines

Development of catalytic amide bond formation reactions from readily available starting materials remains a challenging task for modern organic chemistry. Herein, we report that unactivated carboxylic esters and amines react in the presence of 10 mol % of zirconocene dichloride (Cp2ZrCl2) in toluene at 110 °C to afford amides in very good to excellent conversions. The Zr-catalyzed reaction is amenable for the amidation of aliphatic and aromatic carboxylic esters with primary and secondary amines. The reaction proceeds with almost complete retention of configuration for chiral esters and chiral amines.

Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.

Direct amide formation using radiofrequency heating

We present a simple method for direct and solvent-free formation of amides from carboxylic acids and amines using radiofrequency heating. The direct energy coupling of the AC magnetic field via nickel ferrite magnetic nanoparticles enables fast and controllable heating, as well as enabling facile work-up via magnetic separation.

Direct amide coupling of non-activated carboxylic acids and amines catalysed by zirconium(IV) chloride

Amidst the green: A green, mild and effective protocol for the direct formation of secondary and tertiary amides from non-activated carboxylic acids and amines in good to excellent yields by employing ZrCl4 as the catalyst is presented (see scheme). The amide coupling protocol proved to be suitable for scaled up syntheses, and the mild reaction conditions conserve the enantiopurity of chiral starting materials. Copyright

Synthesis, physical-chemical characterisation and biological evaluation of novel 2-amido-3-hydroxypyridin-4(1H)-ones: Iron chelators with the potential for treating Alzheimer's disease

A novel class of 2-amido-3-hydroxypyridin-4-one iron chelators is described. These compounds have been designed to behave as suitable molecular probes which will improve our knowledge of the role of iron in neurodegenerative conditions. Neurodegenerative disorders, such as Alzheimer's disease (AD) and Parkinson disease (PD), can be considered as diverse pathological conditions sharing critical metabolic processes such as protein aggregation and oxidative stress. Interestingly, both these metabolic alterations seem to be associated with the involvement of metal ions, including iron. Iron chelation is therefore a potential therapeutic approach. The physico-chemical (pKa, pFe 3+ and log P) and biological properties (inhibition of iron-containing enzymes) of these chelators have been investigated in order to obtain a suitable profile for the treatment of neurodegenerative conditions. Studies with neuronal cell cultures confirm that the new iron chelators are neuroprotective against β-amyloid-induced toxicity.

Catalyst and solvent-free amidation of inactive esters of N-protected amino acids

A catalyst free procedure for the preparation of amides from inactive esters of N-protected amino acids and various amines is demonstrated under mild reaction conditions. Our effort to recover excess amine and generated alcohol is an approach towards environment friendly and cost effective synthesis under easy operational conditions.

Facile amide formation via S -nitrosothioacids

Here we report a novel amide bond formation strategy from simple thioacid and amine starting materials. The reaction is mediated by unstable but very reactive S-nitrosothioacid intermediates. This fast reaction under mild conditions should be useful in synthesis.(Figure Presented)