152753-57-6

Basic information

• Product Name: (S)-1-benzylcarbamoyl-2-phenyl-ethanol
• Synonyms: (S)-1-benzylcarbamoyl-2-phenyl-ethanol
• CAS NO: 152753-57-6
• Molecular Weight: 255.316
• Mol File: 152753-57-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-1-benzylcarbamoyl-2-phenyl-ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-benzylcarbamoyl-2-phenyl-ethanol(152753-57-6)
• EPA Substance Registry System: (S)-1-benzylcarbamoyl-2-phenyl-ethanol(152753-57-6)

Safety Data

• Hazardous Substances Data: 152753-57-6(Hazardous Substances Data)

Upstream product

• 86863-62-9 (3S,4R)-1-Benzyl-3-benzyloxy-4-phenyl-azetidin-2-one 
• 828-01-3 phenyllactic acid 
• 100-46-9 benzylamine 
• 88333-03-3 Benzyl isocyanide 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 431069-60-2 3-(Acetyl-methyl-amino)-2-diazo-3-oxo-propionic acid (S)-1-benzylcarbamoyl-2-phenyl-ethyl ester 

Relevant articles and documents

Copper-catalyzed oxidative cleavage of Passerini and Ugi adducts in basic medium yielding α-ketoamides

The aerobic oxidative cleavage of Passerini and Ugi adducts in the presence of base and copper(i) iodide is studied in detail. The oxidative cleavage yields α-ketoamides along with acids and amides from Passerini and Ugi adducts respectively. Mechanistic investigations revealed that the reaction proceeds via a radical pathway involving molecular oxygen. Control experiments with 18O-labeled Passerini adducts confirmed that molecular oxygen is the source of oxygen in α-ketoamides. A variety of Passerini and Ugi adducts were studied to explore the effect of substitution. Overall, the present study provides an insight into the reactivity of Passerini and Ugi adducts in strong basic conditions along with a method to prepare α-ketoamides.

Microwave-assisted rapid and simplified hydrogenation

Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 °C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 °C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of β-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters. Cleavage of the β-lactam ring by hydrogenolysis of the N-C4 bond of 4- aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.