(R)-(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate

Base Information

• Chemical Name: (R)-(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate
• CAS No.: 858344-36-2
• Molecular Formula: C15H19FN2O6S
• Molecular Weight: 374.39
• Hs Code.: 2934999090
• UNII: D02QUU2JKY
• DSSTox Substance ID: DTXSID70442918
• Wikidata: Q72475047
• Mol file: 858344-36-2.mol

Synonyms:174649-09-3;(R)-(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate;(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl methanesulfonate;Linezolid mesylate ester;D02QUU2JKY;[(5R)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate;(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate, (R)-;(5R)-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-5-(((methylsulfonyl)oxy)methyl)-2-oxazolidinone;(5R)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-Oxazolidinone;2-Oxazolidinone, 3-(3-fluoro-4-(4-morpholinyl)phenyl)-5-(((methylsulfonyl)oxy)methyl)-, (R)-;2-Oxazolidinone, 3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-, (5R)-;C15H19FN2O6S;UNII-D02QUU2JKY;SCHEMBL12126884;DTXSID70442918;UCVIKCGVGWBTTI-GFCCVEGCSA-N;MFCD18070719;AKOS015913626;DS-3714;(R)-(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methylmethanesulfonate;AM20030162;CS-0150118;D78062;A851827;J-502106;((R)-3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate;(5R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl]methyl Methanesulfonate;(R)-[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methylmethanesulfonate;{(5R)-3-[3-Fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl methanesulfonate;2-Oxazolidinone, 3-[3-fluoro-4-(4-morpholinyl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-, (5R);methyl ((R)-3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methanesulfonate

Chemical Property of (R)-(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate

Chemical Property:

• PSA: 93.76000
• Density: 1.418
• LogP: 2.17450
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 374.09478567
• Heavy Atom Count: 25
• Complexity: 577

Purity/Quality:

97% ^*data from raw suppliers

(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methylmethanesulfonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)OCC1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCOCC3)F
• Isomeric SMILES: CS(=O)(=O)OC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCOCC3)F

Technology Process of (R)-(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate

There total 6 articles about (R)-(3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl methanesulfonate 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: 96.0%

methanesulfonyl chloride (124-63-0) + 3-(3-fluoro-4-morpholin-4-yl-phenyl)-5-hydroxymethyl-oxazolidin-2-one (513068-96-7) → methanesulfonic acid 3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-oxazolidin-5-ylmethyl ester (858344-36-2,2180621-71-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.5012/bkcs.2012.33.4.1389

Reference yield:

3-fluoro-4-(morpholinyl)aniline (93246-53-8) → methanesulfonic acid 3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-oxazolidin-5-ylmethyl ester (858344-36-2,2180621-71-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: HNO₂

1.2: copper(I) bromide; HBr

2.1: 85 percent / copper(I) iodide; potassium carbonate; (+/-)-trans-1,2-diaminocyclohexane / dioxane / 15 h / 110 °C

3.1: 80 percent / pyridinium p-toluenesulfonate / ethanol / 0.5 h / Heating

4.1: triethylamine / CH₂Cl₂ / 1 h / 0 - 25 °C

With copper(l) iodide; (S,S)-1,2-diaminocyclohexane; pyridinium p-toluenesulfonate; cis-nitrous acid; potassium carbonate; triethylamine; In 1,4-dioxane; ethanol; dichloromethane; 1.2: Sandmeyer reaction / 2.1: Goldberg coupling;

DOI:10.1021/ol026902h

Reference yield:

4-(4-bromo-2-fluorophenyl)morpholine (513068-89-8) → methanesulfonic acid 3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-oxazolidin-5-ylmethyl ester (858344-36-2,2180621-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / copper(I) iodide; potassium carbonate; (+/-)-trans-1,2-diaminocyclohexane / dioxane / 15 h / 110 °C

2: 80 percent / pyridinium p-toluenesulfonate / ethanol / 0.5 h / Heating

3: triethylamine / CH₂Cl₂ / 1 h / 0 - 25 °C

With copper(l) iodide; (S,S)-1,2-diaminocyclohexane; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; In 1,4-dioxane; ethanol; dichloromethane; 1: Goldberg coupling;

DOI:10.1021/ol026902h

upstream raw materials:

methanesulfonyl chloride

3-(3-fluoro-4-morpholin-4-yl-phenyl)-5-hydroxymethyl-oxazolidin-2-one

3-fluoro-4-(morpholinyl)aniline

4-(4-bromo-2-fluorophenyl)morpholine

Downstream raw materials:

linezolid

3-(3-fluoro-4-morpholinophenyl)-5-((3-oxoisothiazol-2(3H)-yl)methyl)oxazolidin-2-one

(S)-[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]aminomethane

(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine