154590-62-2

Basic information

• Product Name: (R)-tert-butyl 4-(2-fluoro-4-(5-(hydroxyMethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate
• Synonyms: (R)-tert-butyl 4-(2-fluoro-4-(5-(hydroxyMethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate
• CAS NO: 154590-62-2
• Molecular Formula: C₁₉H₂₆FN₃O₅
• Molecular Weight: 395.4252432
• Mol File: 154590-62-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 130-131 °C
• Boiling Point: 552.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.297±0.06 g/cm3(Predicted)
• PKA: 14.05±0.10(Predicted)
• CAS DataBase Reference: (R)-tert-butyl 4-(2-fluoro-4-(5-(hydroxyMethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-tert-butyl 4-(2-fluoro-4-(5-(hydroxyMethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate(154590-62-2)
• EPA Substance Registry System: (R)-tert-butyl 4-(2-fluoro-4-(5-(hydroxyMethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate(154590-62-2)

Safety Data

• Hazardous Substances Data: 154590-62-2(Hazardous Substances Data)

Usage

Description

(R)-tert-butyl 4-(2-fluoro-4-(5-(hydroxyMethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate is a complex chemical compound characterized by its unique molecular structure. It features a piperazine ring, a phenyl group, and an oxazolidin-3-yl moiety, along with a tert-butyl 1-carboxylate. The incorporation of a fluorine atom and a hydroxymethyl group contributes to its chemical diversity, potentially allowing it to interact with specific biological pathways or receptors.

Uses

Used in Medicinal Chemistry:
(R)-tert-butyl 4-(2-fluoro-4-(5-(hydroxyMethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate is used as a compound in medicinal chemistry for its potential to target specific biological pathways or receptors due to its unique structure.
Used in Drug Development:
In the field of drug development, (R)-tert-butyl 4-(2-fluoro-4-(5-(hydroxyMethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate is used as a candidate molecule for the development of new drugs, given its structural diversity and potential to interact with biological targets.

Upstream product

• 154590-36-0 tert-butyl 4-(4-(benzyloxycarbonyl)-2-fluorophenyl)piperazine-1-carboxylate 
• 60456-26-0 (R)-glycidyl butyrate 
• 154590-35-9 tert-butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate 
• 154590-34-8 4-(2-fluoro-4-nitrophenyl)-piperazine-1-carboxylic acid tert butyl ester 
• 369-34-6 3,4-difluoronitrobenzene 
• 154590-33-7 1-(2-fluoro-4-nitrophenyl)piperazine 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 

Downstream Products

• 268209-15-0 tert-butyl 4-(4-((S)-5-(aminomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate 
• 154590-63-3 [N-3-(1-tert-butoxycarbonyl)-4-(2-fluoro-4-piperazinyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate 
• 885013-10-5 tert-butyl 4-(2-fluoro-4-{(5R)-2-oxo-5-[(pyrazin-2-yloxy)methyl]-1,3-oxazolidin-3-yl}phenyl)piperazine-1-carboxylate 
• 885013-17-2 tert-butyl 4-(4-{(5R)-5-[(acetyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}-2-fluorophenyl)piperazine-1-carboxylate 
• 252279-84-8 (5R)-3-(3-fluoro-4-piperazin-1-ylphenyl)-5-[(isoxazol-3-yloxy)methyl]-1,3-oxazolidin-2-one 
• 885012-90-8 (5R)-3-{3-fluoro-4-[4-(5-nitro-2-thienyl)piperazin-1-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazolidin-2-one 

Relevant articles and documents

RETRACTED ARTICLE: Design, synthesis of novel oxazolidino-amides/sulfonamides conjugates and their impact on antibacterial activity

Abstract: In view of generating new compounds for future drug development, we have synthesized oxazolidinones library of aryl amides and aryl sulfonamide derivatives. These compounds were screened in vitro against panel of susceptible and resistant Gram-p

Syntheses and antibacterial activity studies of new oxazolidinones from nitroso Diels-Alder chemistry

A series of novel oxazolidinone antibiotics having [2.2.1] and [2.2.2] bicyclic oxazine moieties at the C-5 side chain of the A-ring was synthesized by nitroso Diels-Alder reactions, from three linezolid analogs containing morpholine, piperazine and thiomorpholine, respectively, as the C-ring components. Subsequent N-O bond cleavage generated oxazolidinones with 4-amino cyclo-2-en-1-ol substituents. The in vitro antibacterial activities of these oxazolidinone analogs were evaluated.

Discovery of the novel antithrombotic agent 5-chloro-N-({(5S)-2-oxo-3-[4- (3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide (BAY 59-7939): An oral, direct factor Xa inhibitor

Despite recent progress in antithrombotic therapy, there is still an unmet medical need for safe and orally available anticoagulants. The coagulation enzyme Factor Xa (FXa) is a particularly promising target, and recent efforts in this field have focused on the identification of small-molecule inhibitors with good oral bioavailability. We identified oxazolidinone derivatives as a new class of potent FXa inhibitors. Lead optimization led to the discovery of BAY 59-7939 (5), a highly potent and selective, direct FXa inhibitor with excellent in vivo antithrombotic activity. The X-ray crystal structure of 5 in complex with human FXa clarified the binding mode and the stringent requirements for high affinity. The interaction of the neutral ligand chlorothiophene in the S1 subsite allows for the combination of good oral bioavailability and high potency for nonbasic 5. Compound 5 is currently under clinical development for the prevention and treatment of thromboembolic diseases.