Eperezolid

Base Information

• Chemical Name: Eperezolid
• CAS No.: 165800-04-4
• Molecular Formula: C18H23 F N4 O5
• Molecular Weight: 394.403
• Hs Code.: 2934999090
• UNII: C460ZSU1OW
• DSSTox Substance ID: DTXSID50168028
• Nikkaji Number: J709.721B
• Wikipedia: Eperezolid
• Wikidata: Q1346746
• NCI Thesaurus Code: C81444
• ChEMBL ID: CHEMBL47955
• Mol file: 165800-04-4.mol

Synonyms:eperezolid;N-((3-(3-fluoro-4-(N-1-(4-hydroxyacetyl)piperazinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide;U 100592;U-100592

Chemical Property of Eperezolid

Chemical Property:

• Vapor Pressure: 1.22E-20mmHg at 25°C
• Melting Point: 174-176℃
• Boiling Point: 701.2°C at 760 mmHg
• PKA: 13.84±0.10(Predicted)
• Flash Point: 377.9°C
• PSA: 102.42000
• Density: 1.37g/cm³
• LogP: 0.38670
• Storage Temp.: 2-8°C
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥14.05 mg/mL in DMSO
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 394.16524801
• Heavy Atom Count: 28
• Complexity: 599

Purity/Quality:

97% ^*data from raw suppliers

Eperezolid-d3 ^*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)N3CCN(CC3)C(=O)CO)F
• Isomeric SMILES: CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCN(CC3)C(=O)CO)F
• Uses: Antibacterial. Eperezolid is an antimicrobial.

Technology Process of Eperezolid

There total 20 articles about Eperezolid 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: 89.0%

N-((S)-3-{4-[4-(2-Benzyloxy-acetyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide (174649-08-2) → eperezolid (165800-04-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; dichloromethane; under 760 Torr;

DOI:10.1016/j.tetlet.2006.07.065

Reference yield: 73.0%

Benzyloxyacetyl chloride (19810-31-2) + (S)-N-[[3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (174649-06-0) → eperezolid (165800-04-4)

Guidance literature:

(S)-N-[[3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide; With methanol; palladium on activated charcoal; In ethyl acetate; at 20 ℃;

Benzyloxyacetyl chloride; With triethylamine; In dichloromethane; at 0 - 20 ℃;

With hydrogen; palladium on activated charcoal; In methanol; Further stages.;

DOI:10.1002/hc.20435

Reference yield:

(S)-N-[[3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (174649-06-0) → eperezolid (165800-04-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / H₂ / Pd/C / methanol; CH₂Cl₂ / 760 Torr

2: 100 percent / Et₃N / CH₂Cl₂ / 0 °C

3: 89 percent / H₂ / Pd/C / methanol; CH₂Cl₂ / 760 Torr

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1016/j.tetlet.2006.07.065

upstream raw materials:

N-((S)-3-{4-[4-(2-Benzyloxy-acetyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide

tiolacetic acid

(R)-5-Azidomethyl-3-{3-fluoro-4-[4-(2-hydroxy-acetyl)-piperazin-1-yl]-phenyl}-oxazolidin-2-one

(S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Downstream raw materials:

4-{4-[benzyloxycarbonyl-(3-oxo-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester

4-{4-[benzyloxycarbonyl-(3-hydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester

4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester

(R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol