Radezolid

Base Information

• Chemical Name: Radezolid
• CAS No.: 869884-78-6
• Molecular Formula: C22H23FN6O3
• Molecular Weight: 438.461
• UNII: 53PC6LO35W
• DSSTox Substance ID: DTXSID301007238
• Wikipedia: Radezolid
• Wikidata: Q7280139
• NCI Thesaurus Code: C81442
• Metabolomics Workbench ID: 153345
• ChEMBL ID: CHEMBL455461
• Mol file: 869884-78-6.mol

Synonyms:N-((3-(2-fluoro-4'-(((1H-1,2,3-triazol-5-ylmethyl)amino)methyl)(1,1'-biphenyl)-4-yl)-2-oxo-5-oxazolidinyl)methyl)acetamide;radezolid;RX 1741;RX-1741;RX1741

Chemical Property of Radezolid

Chemical Property:

• Appearance/Colour: White to off-white solid
• Boiling Point: 712.5±60.0 °C(Predicted)
• PKA: 15.53±0.46(Predicted)
• PSA: 112.24000
• Density: 1.336 g/cm³
• LogP: 3.20870
• Solubility.: ≥43.8 mg/mL in DMSO; insoluble in H2O; ≥18.08 mg/mL in EtOH with gentle warming
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 438.18156678
• Heavy Atom Count: 32
• Complexity: 647

Purity/Quality:

98%Min ^*data from raw suppliers

Radezolid >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NCC1CN(C(=O)O1)C2=CC(=C(C=C2)C3=CC=C(C=C3)CNCC4=NNN=C4)F
• Isomeric SMILES: CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)C3=CC=C(C=C3)CNCC4=NNN=C4)F
• Recent ClinicalTrials: Safety and Efficacy Study of Oxazolidinone to Treat Pneumonia

Technology Process of Radezolid

There total 9 articles about Radezolid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(5S)-N-{3-[2-fluoro-4'-({[1-(4-methoxybenzyl)-1H-[1,2,3]triazol-4-ylmethyl]amino}methyl)biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}acetamide hydrochloride (916888-21-6) → (5S)-N-[3-(2-fluoro-4'-{[(1H-[1,2,3]triazol-4-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-oxazolidin-5-ylmethyl]acetamide (869884-78-6)

Guidance literature:

(5S)-N-{3-[2-fluoro-4'-({[1-(4-methoxybenzyl)-1H-[1,2,3]triazol-4-ylmethyl]amino}methyl)biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}acetamide hydrochloride; With (5S)-N-{3-[2-fluoro-4'-({[1-(4-methoxybenzyl)-1H-[1,2,3]triazol-5-ylmethyl]amino}methyl)biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}acetamide hydrochloride; trifluoroacetic acid; at 65 - 70 ℃; for 12h;

With sodium carbonate; In water; ethyl acetate; at 20 ℃; for 1h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 1-(azidomethyl)-4-methoxybenzene (70978-37-9) + 4-formylphenylboronic acid, (87199-17-5) + Propargylamine (2450-71-7) + (S)-N-[3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidine-5-ylmethyl]acetamide (149524-45-8) → (5S)-N-[3-(2-fluoro-4'-{[(1H-[1,2,3]triazol-4-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-oxazolidin-5-ylmethyl]acetamide (869884-78-6)

Guidance literature:

1-(azidomethyl)-4-methoxybenzene; Propargylamine; In toluene; at 25 - 110 ℃; for 21h;

4-formylphenylboronic acid,; In 1,2-dichloro-ethane; at 25 ℃; for 0.166667h;

di-tert-butyl dicarbonate; (S)-N-[3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidine-5-ylmethyl]acetamide; Further stages;

Reference yield:

C27H31FN6O5 → (5S)-N-[3-(2-fluoro-4'-{[(1H-[1,2,3]triazol-4-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-oxazolidin-5-ylmethyl]acetamide (869884-78-6)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1016/j.bmcl.2008.10.011

upstream raw materials:

(5S)-N-{3-[2-fluoro-4'-({[1-(4-methoxybenzyl)-1H-[1,2,3]triazol-4-ylmethyl]amino}methyl)biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}acetamide hydrochloride

meta-fluoroaniline

di-tert-butyl dicarbonate

1-(azidomethyl)-4-methoxybenzene

Downstream raw materials:

(5S)-N-[3-(2-fluoro-4'-{[(1H-[1,2,3]triazol-4-ylmethyl)amino]methyl}biphenyl-4-yl)-2-oxo-oxazolidin-5-ylmethyl]acetamide hydrochloride

Refernces

• 1、 -. "Process for the synthesis of triazoles". Page/Page column 35. . Retrieved 2010/09/18.