Torezolid

Base Information

• Chemical Name: Torezolid
• CAS No.: 856866-72-3
• Molecular Formula: C17H15FN6O3
• Molecular Weight: 370.343
• Hs Code.: 29339900
• European Community (EC) Number: 815-370-6
• UNII: 97HLQ82NGL
• DSSTox Substance ID: DTXSID10234975
• Nikkaji Number: J3.050.870J
• Wikipedia: Tedizolid
• Wikidata: Q7825683
• NCI Thesaurus Code: C84222
• RXCUI: 1540825
• Metabolomics Workbench ID: 154963
• ChEMBL ID: CHEMBL1257051
• Mol file: 856866-72-3.mol

Synonyms:Torezolid

Chemical Property of Torezolid

Chemical Property:

• Melting Point: 201 °C
• Boiling Point: 614.5±65.0 °C(Predicted)
• PKA: 14.05±0.10(Predicted)
• PSA: 106.26000
• Density: 1.57
• LogP: 1.46070
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Water (Slightly, Heated)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 370.11896652
• Heavy Atom Count: 27
• Complexity: 543

Purity/Quality:

99.5%+ ^*data from raw suppliers

Tedizolid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiinfective Agents
• Canonical SMILES: CN1N=C(N=N1)C2=NC=C(C=C2)C3=C(C=C(C=C3)N4CC(OC4=O)CO)F
• Isomeric SMILES: CN1N=C(N=N1)C2=NC=C(C=C2)C3=C(C=C(C=C3)N4C[C@@H](OC4=O)CO)F
• Recent ClinicalTrials: Oral Antimicrobial Treatment vs. Outpatient Parenteral for Infective Endocarditis
• Recent EU Clinical Trials: Oral antimicrobial treatment vs. outpatient parenteral for infective
• Indications: Tedizolid phosphate is an oxazolidinone compound used in the treatment of acute bacterial skin and skin structure infections caused by the following gram-positive bacteria-sensitive strains: Staphylococcus aureus (including Methicillin-resistant and methicillin-susceptible strains), pyogenic streptococci, Streptococcus lactis, Streptococcus angustifolia (including Angina, Streptococcus intermedius and Streptococcus constellation), and Enterococcus faecalis.

Technology Process of Torezolid

There total 25 articles about Torezolid 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: 99.0%

C23H29FN6O3Si → (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one (856866-72-3)

Guidance literature:

With cesium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

Reference yield: 95.0%

3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester (1220910-89-3) → (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one (856866-72-3)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert.-butyl lithium; (R)-glycidyl butyrate; In tetrahydrofuran; at 0 - 30 ℃; for 15h; Reagent/catalyst; Large scale;

Reference yield: 86.7%

3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester (1220910-89-3) + (R)-glycidyl butyrate (60456-26-0) → (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one (856866-72-3)

Guidance literature:

3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester; With potassium tert-butylate; lithium tert-butoxide; In tetrahydrofuran; acetonitrile; at 25 ℃; for 2h; Inert atmosphere;

(R)-glycidyl butyrate; In tetrahydrofuran; acetonitrile; for 3h;

upstream raw materials:

5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester

(R)-glycidyl butyrate

2,5-dibromopyridine

Downstream raw materials:

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridine-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(azidomethyl)oxazolidin-2-one

(S)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(aminomethyl)oxazolidin-2-one

(S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)-2-methoxyacetamide

Refernces

• 1、 -. "Purification method of tedizolid phosphate". Paragraph 0035. . Retrieved 2021/06/21.
• 2、 -. "Preparation method of high-purity tedizolid phosphate". . . Retrieved 2020/05/30.