4410-32-6

Upstream product

• 4358-87-6 (RS)-methyl mandelate 
• 100-46-9 benzylamine 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 40991-79-5 N,N-dibenzyl-2-oxo-2-phenylacetamide 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 103-80-0 phenylacetyl chloride 
• 88333-03-3 Benzyl isocyanide 
• 100-52-7 benzaldehyde 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 611-73-4 Benzoylformic acid 
• 4870-65-9 2-bromophenylacetic acid 
• 4530-20-5 BOC-glycine 
• 29289-35-8 2-azido-2-phenylacetic acid 
• 81384-43-2 2-(benzylamino)-2-oxo-1-phenylethyl acetate 

Downstream Products

• 28193-70-6 N-benzyl-2-oxo-2-phenylacetamide 
• 110271-94-8 6-[(Z)-Benzylimino]-2-isopropoxy-5-phenyl-5,6-dihydro-[1,3,4]oxadiazine-4-carboxylic acid isopropyl ester 
• 101274-23-1 3-benzyl-5-phenyl-2,4-oxazolidinedione 
• 81384-43-2 2-(benzylamino)-2-oxo-1-phenylethyl acetate 
• 62735-59-5 2-methoxy-N-benzyl-2-phenylethanamide 
• 6109-33-7 4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 
• 1408381-76-9 (4R)-4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 
• 1408382-17-1 (4S)-2-acetyl-4-phenyl-1,4-dihydro-2H-izoquinolin-3-one 
• 1408382-14-8 (4S)-4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 
• 1408382-22-8 (4R)-2-acetyl-4-phenyl-1,4-dihydro-2H-izoquinolin-3-one 
• 1408382-06-8 2-acetyl-4-phenyl-1,4-dihydro-2H-izoquinolin-3-one 
• 89160-45-2 (4R)-(+)-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 88393-58-2 (R)-N-benzyl-2-hydroxy-2-phenylacetamide 
• 82270-62-0 (S)-N-benzylmandelamide 

Relevant academic research and scientific papers

“On-water” reduction of α-keto amide by Hantzsch ester: A chemoselective catalyst- and additive-free way to α-hydroxy amide

An efficient and practical method for chemoselective “on-water” reduction of α-keto amide by Hantzsch ester without using any catalysts and additives was developed. Control experiments indicated that the intramolecular hydrogen bond of α-keto amide was cr

Manganese Catalyzed Direct Amidation of Esters with Amines

The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.

Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines

Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides in good to excellent yields. The improved catalytic activity can be ascribed to the oxygenated functionalities present on the graphene oxide surface which forms H-bonding with the reactants accelerating the reaction. Improved yields and a wide range of functional group tolerance are some of the important features of the developed protocol.

Homogeneous Hydrogenation with a Cobalt/Tetraphosphine Catalyst: A Superior Hydride Donor for Polar Double Bonds and N-Heteroarenes

The development of catalysts based on earth abundant metals in place of noble metals is becoming a central topic of catalysis. We herein report a cobalt/tetraphosphine complex-catalyzed homogeneous hydrogenation of polar unsaturated compounds using an air- and moisture-stable and scalable precatalyst. By activation with potassium hydroxide, this cobalt system shows both high efficiency (up to 24 000 TON and 12 000 h-1 TOF) and excellent chemoselectivities with various aldehydes, ketones, imines, and even N-heteroarenes. The preference for 1,2-reduction over 1,4-reduction makes this method an efficient way to prepare allylic alcohols and amines. Meanwhile, efficient hydrogenation of the challenging N-heteroarenes is also furnished with excellent functional group tolerance. Mechanistic studies and control experiments demonstrated that a CoIH complex functions as a strong hydride donor in the catalytic cycle. Each cobalt intermediate on the catalytic cycle was characterized, and a plausible outer-sphere mechanism was proposed. Noteworthy, external inorganic base plays multiple roles in this reaction and functions in almost every step of the catalytic cycle.

Catalyst- and Additive-Free Chemoselective Transfer Hydrogenation of α-Keto Amides to α-Hydroxy Amides by Sodium Formate

A catalyst- and additive-free chemoselective transfer hydrogenation of α-keto amides to α-hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram-scale synthesis and transformation of the resultant α-hydroxy amides into polysubstituted acetamides and 2-arylindole derivatives. Control experiments suggest that the NH group of α-keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.

Method for synthesizing chiral alpha-hydroxy amide by catalyzing prochiral alpha-keto-amide

The invention provides a novel method for preparing chiral alpha-hydroxy amide through asymmetric hydrogenation of pro-chiral alpha-keto-amide using a novel tridentate nitrogen phosphine ligand to prepare a series of chiral alpha-hydroxy amide compounds.

REAGENTS AND METHODS FOR ESTERIFICATION

Methods and reagents for esterification of biological molecules including proteins, polypeptides and peptides. Diazo compounds of formula (I): where R is hydrogen, an alkyl, an alkenyl or an alkynyl, RA represents 1-5 substituents on the indicated phenyl ring and RM is an organic group, which includes a label, a cell penetrating group, a cell targeting group, or a reactive group or latent reactive group for reaction to bond to a label, a cell penetrating group, or a cell targeting group, among other organic groups are useful for esterification of biological molecules. Also provided are diazo compounds which are bifunctional and trifunctional coupling reagents as well as reagents for the synthesis of compounds of formula (I).

A Heterogeneous Niobium(V) Oxide Catalyst for the Direct Amidation of Esters

This study reports the first example of a heterogeneous catalytic system for the direct amidation of various esters with amines. Of 25 types of catalyst, Nb2O5 shows the highest activity in the amidation of methyl benzoate with aniline. Nb2O5 gives high yields in the amidation of various esters and amines under solvent-free conditions, is reusable, and shows higher turnover numbers than previously reported homogeneous catalysts such as La(OTf)3. IR spectroscopic studies of ethyl acetate adsorbed on the catalysts show a strong acid-base interaction between the Nb5+ Lewis acid site and carbonyl oxygen, which can result in high reactivity of the ester with a nucleophile (amine) and, thus, high activity of Nb2O5. Kinetic results show that the activity of Nb2O5 does not markedly decrease with increasing aniline concentration, in contrast to reference catalysts TiO2 and La(OTf)3. The relatively low negative impact of basic molecules on the Lewis acid catalysis of Nb2O5 also enables its high activity.

Optimized Diazo Scaffold for Protein Esterification

The O-alkylation of carboxylic acids with diazo compounds provides a means to esterify carboxylic acids in aqueous solution. A Hammett analysis of the reactivity of diazo compounds derived from phenylglycinamide revealed that the (p-methylphenyl)-glycinamide scaffold has an especially high reaction rate and ester/alcohol product ratio and esterifies protein carboxyl groups more efficiently than any known reagent. (Chemical Equation Presented).

Chemoselective reduction of α-keto amides using nickel catalysts

Ni-catalysts are used for the first time to synthesize highly important α-hydroxy amides and β-amino alcohols from α-keto amides by chemoselective and complete reduction using hydrosilanes. Chemoselective complete reduction of α-keto amides in the presenc