(S)-2-((3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione

Base Information

• Chemical Name: (S)-2-((3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione
• CAS No.: 168828-89-5
• Molecular Formula: C22H20FN3O5
• Molecular Weight: 425.416
• UNII: BW94IJR3DS
• DSSTox Substance ID: DTXSID20514250
• Wikidata: Q72475061
• Mol file: 168828-89-5.mol

Synonyms:168828-89-5;(S)-2-((3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione;Linezolid Desacetamide Phthalimide;Deacetamide Linezolid Phthalimide;BW94IJR3DS;2-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione;(S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide;(S)-2-((3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazol-idin-5-yl)methyl)isoindoline-1,3-dione;(S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide;2-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-1H-Isoindole-1,3(2H)-dione;FKZUTWSVQLXKQE-OAHLLOKOSA-N;UNII-BW94IJR3DS;SCHEMBL3295262;DTXSID20514250;AKOS015901855;AM20030128;A25090;J-502507;((S )-N-((3-(3-Fluoro-4-( 4-morpholinyl)phenyl)-2-oxo-5-xazolidinyl)methyl)phthalimide);(R)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide;(S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl];N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide, (S)-;1H-Isoindole-1,3(2H)-dione, 2-(((5S)-3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)-;1H-Isoindole-1,3(2H)-dione, 2-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-, (S)-;2-({(5S)-3-[3-Fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione

Chemical Property of (S)-2-((3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione

Chemical Property:

• Melting Point: 205-207 °C
• Boiling Point: 619.13 °C at 760 mmHg
• PKA: 5.73±0.40(Predicted)
• Flash Point: 328.238 °C
• PSA: 79.39000
• Density: 1.441 g/cm³
• LogP: 2.35160
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly, Sonicated), Chloroform (Slightly), DMSO (Slightly), Meth
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 425.13869891
• Heavy Atom Count: 31
• Complexity: 706

Purity/Quality:

99.5% ^*data from raw suppliers

DeacetamideLinezolidPhthalimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C2=C(C=C(C=C2)N3CC(OC3=O)CN4C(=O)C5=CC=CC=C5C4=O)F
• Isomeric SMILES: C1COCCN1C2=C(C=C(C=C2)N3C[C@@H](OC3=O)CN4C(=O)C5=CC=CC=C5C4=O)F
• Uses: Linezolid (L466500) intermediate.

Technology Process of (S)-2-((3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione

There total 27 articles about (S)-2-((3-(3-Fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione 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: 96.51%

3-fluoro-4-(morpholin-4-yl)-phenyl isocyanate (224323-51-7) + (S)-N-glycidylphthalimide (161596-47-0) → 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione (168828-89-5,947736-16-5)

Guidance literature:

With lithium bromide; at 120 ℃; for 4h; Temperature; Solvent;

Reference yield: 92.8%

2-[(5R)-(2-oxo-5-oxazolidinyl)-methyl]-1H-isoindole-1,3(2H)-dione (352524-58-4) + 4-(4-bromo-2-fluorophenyl)morpholine (513068-89-8) → 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione (168828-89-5,947736-16-5)

Guidance literature:

With copper(l) iodide; N,N-dimethyl-ethanamine; potassium carbonate; In dichloromethane; at 110 ℃; for 20h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 92.0%

(5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone + potassium phtalimide (1074-82-4) → 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione (168828-89-5,947736-16-5)

Guidance literature:

at 140 - 145 ℃; for 2h;

DOI:10.2174/1570178614666161230163455

upstream raw materials:

N-[3-phthalimido-2-(R)-hydroxypropyl]-3-fluoro-4-(4-morpholinyl)aniline

1,1'-carbonyldiimidazole

potassium phtalimide

phthalimide

Downstream raw materials:

linezolid

(S)-N-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]benzamide

4-amino-5-(ethylsulfonyl)-N-(S)-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-2-methoxybenzamide

5-(aminosulfonyl)-N-(S)-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-2-methoxy benzamide

Refernces

• 1、 -. "ONE POT SYNTHESIS FOR THE PREPARATION OF SUBSTITUTED PHTHALIMIDO OXAZOLIDINONE ANTIBACTERIALS AND OXAZOLIDINONE ANTIHAROMBOTICS COMPOUNDS BY USING RECYCLABLE HETEROGENEOUS CATALYST". Page/Page column 10-11. . Retrieved 2018/04/20.
• 2、 -. "Process for the preparation of linezolid". . . Retrieved 2017/05/31.