292858-05-0

Basic information

• Product Name: Benzenebutanoic acid, b-bromo-a-oxo-, ethyl ester
• Synonyms: ethyl 3-bromo-2-oxo-4-phenylbutyrate
• CAS NO: 292858-05-0
• Molecular Formula: C12H13BrO3
• Molecular Weight: 285.137
• Mol File: 292858-05-0.mol

Chemical Properties

• Boiling Point: 335.9±35.0 °C(Predicted)
• Density: 1.408±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzenebutanoic acid, b-bromo-a-oxo-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenebutanoic acid, b-bromo-a-oxo-, ethyl ester(292858-05-0)
• EPA Substance Registry System: Benzenebutanoic acid, b-bromo-a-oxo-, ethyl ester(292858-05-0)

Safety Data

• Hazardous Substances Data: 292858-05-0(Hazardous Substances Data)

Upstream product

• 64920-29-2 2-oxo-4-phenylbutanoic acid ethyl ester 

Downstream Products

• 292858-06-1 ethyl 3-benzylimidazo[1,2-a]pyridine-2-carboxylate 
• 204376-35-2 ethyl 5-benzyl-2-oxo-2,3-dihydrooxazole-4-carboxylate 
• 869012-75-9 ethyl (2S,3S)-3-bromo-2-hydroxy-4-phenylbutanoate 
• 869012-78-2 ethyl (2R,3R)-3-phenyl-2,3-oxiranebutanoate 
• 869012-80-6 ethyl (4S,5R)-4-benzyl-2-methyl-4,5-dihydrooxazole-5-carboxylate 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 742109-00-8 ethyl (2R,3S)-3-acetylamino-2-hydroxy-4-phenylbutanoate 
• 77505-86-3 ethyl 2-amino-5-benzyl-1,3-thiazole-4-carboxylate 
• 1342804-17-4 ethyl 5-benzyl-2-(2,5-difluorophenyl)oxazole-4-carboxylate 
• 1342803-89-7 (R)-N-((5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)methylene)-2-methylpropane-2-sulfinamide 
• 1342803-91-1 (R)-N-((R)-1-(5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)-2,2-dimethylpropyl)-2-methylpropane-2-sulfinamide 
• 1342804-48-1 (R)-1-(5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)-2,2-dimethylpropan-1-amine 
• 1342804-03-8 (3R,4R)-benzyl 3-(((R)-1-(5-benzyl-2-(2,5-difiuorophenyl)thiazol-4-yl)-2,2-dimethylpropylamino)methyl)-4-fluoropyrrolidine-1-carboxylate 
• 1342804-05-0 (3R,4R)-benzyl 3-(((S)-2-acetoxy-N-((R)-1-(5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)-2,2-dimethylpropyl)propanamido)methyl)-4-fluoropyrrolidine-1-carboxylate 

Relevant articles and documents

Synthesis and SAR study of new thiazole derivatives as vascular adhesion protein-1 (VAP-1) inhibitors for the treatment of diabetic macular edema: Part 2

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Asymmetric bioreduction of ethyl 3-halo-2-oxo-4-phenylbutanoate by Saccharomyces cerevisiae immobilized in Ca-alginate beads with double gel layer

The asymmetric bioreduction of ethyl 3-halo-2-oxo-4-phenylbutanoate was studied for several microorganisms and especially for Saccharomyces cerevisiae. The highest chemical yield (90%), de (70%) and ee (96-99%) were obtained with S. cerevisiae immobilized in calcium alginate beads with double gel layers, and reaction conditions were optimized by changing matrix of immobilization, concentration of substrate, and feeding with glucose as electron donor. The entrapment of cells with double gel layers was fundamental to achieve high enantio- and diastereoselectivity.

THIAZOLE DERIVATIVES HAVING VAP-1 INHIBITORY ACTIVITY

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A highly enantioselective chemoenzymatic synthesis of syn-3-amino-2-hydroxy esters: Key intermediates for taxol side chain and phenylnorstatine

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New methods for the synthesis of 2-oxazolone-4-carboxylates from 3-nosyloxy- and 3-bromo-2-ketoesters are described. Condensation of 3-nosyloxy-2-ketoesters with methyl carbamate in refluxing toluene in the presence of p-TSA provided 2-oxazolone-4-carboxylates in good yields (41-80%). Alternatively, bromination of α-ketoesters with CuBr2 provided 3-bromo-2-ketoesters which condensed with methyl carbamate in the presence of p-TSA and AgOTfunder similar conditions to provide 2-oxazolone-4-carboxylates in comparable yields (30-79%). The 2-oxazolone-4-carboxylates bear functionality that can be elaborated to a variety of potentially useful compounds. For example, some of these heterocycles were readily N-acylated, reduced to alcohols, or saponified and coupled with amino acids.

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