352524-57-3

Basic information

• Product Name: 2-Oxazolidinone, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-, (5R)-
• CAS NO: 352524-57-3
• Molecular Formula: C20H25NO3Si
• Molecular Weight: 355.509
• Mol File: 352524-57-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-, (5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-, (5R)-(352524-57-3)
• EPA Substance Registry System: 2-Oxazolidinone, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-, (5R)-(352524-57-3)

Safety Data

• Hazardous Substances Data: 352524-57-3(Hazardous Substances Data)

Upstream product

• 99-90-1 para-bromoacetophenone 
• 97859-49-9 (R)-5-(hydroxymethyl)-1,3-oxazolidin-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 66211-46-9 (R)-3-amino-1,2-propanediol 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 1427172-27-7 (R)-3-(5-bromopyridin-2-yl)-5-(((tert-butyldiphenylsilyl)oxy)methyl)oxazolidin-2-one 

Relevant articles and documents

Solubility-driven optimization of (pyridin-3-yl) benzoxazinyl- oxazolidinones leading to a promising antibacterial agent

The solubility-driven structural modification of (pyridin-3-yl) benzoxazinyl-oxazolidinones is described, which resulted in the development of a new series of benzoxazinyl-oxazolidinone analogues with high antibacterial activity against Gram-positive pathogens, including that against linezolid-resistant strains and low hERG inhibition. With regard to structure-activity relationship (SAR) trends among the various substituents on the pyridyl ring, relatively small and nonbasic substituents were preferable to sterically demanding or basic substituents. Oxazolidinone ring substitution on the pyridyl ring generated analogues with antibacterial activity superior to imidazolidinone ring. Solubility was enhanced by the incorporation of polar groups, especially when compounds were converted to their prodrugs. Among the prodrugs, compound 85 exhibited excellent solubility and a good pharmacokinetic profile. In a MRSA systemic infection model, compound 85 displayed an ED 50 = 5.00 mg/kg, a potency that is 2-fold better than that of linezolid.

Synthesis of N-arylated oxazolidinones via a palladium catalyzed cross coupling reaction. Application to the synthesis of the antibacterial agent Dup-721

A method for the intermolecular coupling of aryl bromides and oxazolidinones is described. Application to intermediates useful for the preparation of a known class of antibacterial agent and the synthesis of the known antibacterial oxazolidinone Dup-721 are described.