19035-02-0

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 103-71-9 phenyl isocyanate 
• 3422-02-4 N-(benzyloxycarbonyl)aniline 
• 98-80-6 phenylboronic acid 
• 62-53-3 aniline 
• 147253-97-2 (S)-(-)-α-benzyl 1-phenylethylcarbamate 
• 582-61-6 benzoyl azide 
• 65-85-0 benzoic acid 

Downstream Products

• 71053-97-9 (S)-N-phenyl-N'-(1-phenylethyl)carbodiimide 
• 53669-92-4 1-(4-Chloro-phenyl)-3-((S)-1-phenyl-ethyl)-urea 

Relevant academic research and scientific papers

Efficient Direct Halogenation of Unsymmetrical N -Benzyl- and N -Phenylureas with Trihaloisocyanuric Acids

A simple and efficient methodology for the direct halogenation of N -phenylureas was developed using trihaloisocyanuric acids in acetonitrile at room temperature. This protocol proved to be effective for the construction of N -phenylureas with different patterns of substitution. Additionally, less reactive N -benzylureas were halogenated in the presence of a mixture of trifluoroacetic acid and acetonitrile at room temperature.

Preferred Binding of Carboxylates by Chiral Urea Derivatives Containing α-Phenylethyl Group

An efficient, simple protocol for the synthesis of a new family of chiral ureas 1 – 4 is described. The binding properties of 1 – 4 toward different anion (acetate, benzoate, fluoride, and chloride) have been studied by1H-NMR titration and have been observed in the case of 4 is a selective receptor for acetate. The theoretical calculation M06/6-311+G(d,p) helped us explain the binding properties observed. The most interesting observation is that this calculated structure is consistent with expected, based on the concept of allylic 1,3-strain (A1,3strain). When chiral caboxylates were studied, urea 1 was the best in discriminating between enantiomers.

Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines

A novel one-pot synthesis of unsymmetrical ureas, carbamates and thiocarbamates from Cbz-protected amines has been developed. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, isocyanates are generated in situ, which facilitate rapid reaction with amines, alcohols, and thiols to afford the corresponding ureas, carbamates and thiocarbamates in high yields.

A Facile and Efficient Method for the Formation of Unsymmetrical Ureas Using DABAL-Me3

A practical synthetic method for the formation of unsymmetrical-substituted ureas is described. The synthesis of the unsymmetrical ureas was readily performed from 2,2,2-trichloroethyl carbamate compounds by treatment of amines with bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane (DABAL-Me3). Using this reaction protocol, various trisubstituted and tetrasubstituted ureas were synthesized in high yields. This study offers a promising approach for the facile synthesis of a variety of unsymmetrical ureas from 2,2,2-trichloroethyl carbamates.

A synthetic approach to N -aryl carbamates via copper-catalyzed Chan-Lam coupling at room temperature

A mild and efficient synthesis of N-arylcarbamates was achieved by reacting azidoformates with boronic acids in the presence of 10 mol % of copper chloride catalyst. The reaction proceeds readily in an open flask at room temperature without additional base, ligand, or additive. Rapid access to urea analogues via a two-step one-pot procedure is enabled by reacting N-arylcarbamates with aluminum-amine complexes. In addition, among several boronic acid derivatives prepared, dimethylphenyl boronate was found to react rapidly in its reaction with benzyl azidoformate, invoking in situ generation of this species in the catalytic cycle.

Discovery and structural modification of 1-phenyl-3-(1-phenylethyl)urea derivatives as inhibitors of complement

A series of 1-phenyl-3-(1-phenylethyl)urea derivatives were identified as novel and potent complement inhibitors through structural modification of the original compound from high-throughput screening. Various analogues (7 and 13-15) were synthesized and identified as complement inhibitors, with the introduction of a five- or six-carbon chain (7c, 7d, 7k, 7l, and 7o) greatly improving their activity. Optimized compound 7l has an excellent inhibition activity with IC50 values as low as 13 nM. We demonstrated that the compound 7l inhibited C9 deposition through the classical, the lectin, and the alternative pathways but had no influence on C3 and C4 depositions.

Chiral self-discrimination of the enantiomers of α-phenylethylamine derivatives in proton NMR

Two types of chiral analytes, the urea and amide derivatives of α-phenylethylamine, were prepared. The effect of inter- molecular hydrogen-bonding interaction on self-discrimination of the enantiomers of analytes has been investigated using high-resolutio

Enantiomerically Pure Guanidine-Catalysed Asymmetric Nitroaldol Reaction

Enantiomerically pure guanidines with and without C2 symmetry have been prepared and used as catalysts in the addition of nitromethane to aldehydes (Henry reaction).The influence of the structure and amount of the guanidine, the solvent and the temperatur