(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.: 174649-09-3
• Molecular Formula: C15H19FN2O6S
• Molecular Weight: 374.39
• Hs Code.: 2934999090
• UNII: D02QUU2JKY
• DSSTox Substance ID: DTXSID70442918
• Wikidata: Q72475047
• Mol file: 174649-09-3.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:

• Melting Point: 183-185oC
• Boiling Point: 592.7±50.0 °C(Predicted)
• PKA: 5.71±0.40(Predicted)
• PSA: 93.76000
• Density: 1.418
• LogP: 2.17450
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)
• 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:

99% ^*data from raw suppliers

(5R)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone ^*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
• Uses: (5R)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone (Linezolid USP Related Compound D) is an intermediate in the synthesis of Linezolid Dimer (L466520), an impurity of the antibacterial agent Linezolid (L466500).

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

There total 17 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: 100.0%

methanesulfonyl chloride (124-63-0) + (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol (168828-82-8) → (R)-methyl methanesulfonate (174649-09-3,2180621-71-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

Reference yield:

3,4-difluoronitrobenzene (369-34-6) → (R)-methyl methanesulfonate (174649-09-3,2180621-71-8)

Guidance literature:

Multi-step reaction with 4 steps

1: N,N-diisopropylethylamine / acetonitrile / 17 h / Heating

2: H₂ / PtO₂ / methanol / 3 h / 20 °C / 1471.02 Torr

3: Et₃N / tetrahydrofuran / 2 h / 20 °C

With hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; platinum(IV) oxide; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1248/cpb.49.353

Reference yield:

3-fluoro-4-(4-morpholinyl)nitrobenzene (2689-39-6) → (R)-methyl methanesulfonate (174649-09-3,2180621-71-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / PtO₂ / methanol / 3 h / 20 °C / 1471.02 Torr

2: Et₃N / tetrahydrofuran / 2 h / 20 °C

With hydrogen; triethylamine; platinum(IV) oxide; In tetrahydrofuran; methanol;

DOI:10.1248/cpb.49.353

upstream raw materials:

methanesulfonyl chloride

(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

(3-fluoro-4-morpholin-4-yl-phenyl)-(3-oxo-propyl)-carbamic acid benzyl ester

(3-fluoro-4-morpholin-4-yl-phenyl)-(3-hydroxy-propyl)-carbamic acid benzyl ester

Downstream raw materials:

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

linezolid

(R)-S-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]thioacetate

2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF CRYSTALLINE FORM I OF LINEZOLID AND ITS COMPOSITIONS". Page/Page column 15. . Retrieved 2015/05/26.
• 2、 -. "PROCESS FOR THE PREPARATION OF CRYSTALLINE LINEZOLID". Page/Page column 16-17. . Retrieved 2013/06/05.