2-[[(5S)-3-(3-Fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]isoindoline-1,3-dione supplier

Name
DeacetaMide Linezolid PhthaliMide
EINECS 1533716-785-6
CAS No. 168828-89-5
Article Data20
CAS DataBase
Density 1.441 g/cm³
Solubility
Melting Point 205-207 °C
Formula C₂₂H₂₀FN₃O₅
Boiling Point 619.13 °C at 760 mmHg
Molecular Weight 425.416
Flash Point 328.238 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5- oxazolidinyl]methyl]phthalimide;2-[[(5S)-3-(3-Fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]isoindoline-1,3-dione;
PSA 79.39000
LogP 2.35160

Synthetic route

: 224323-51-7
3-fluoro-4-(morpholin-4-yl)-phenyl isocyanate

: 161596-47-0
(S)-N-glycidylphthalimide

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
With lithium bromide at 120℃; for 4h; Temperature; Solvent;	96.51%
With lithium bromide In N,N-dimethyl-formamide at 60℃; for 4h; Reagent/catalyst; Solvent;	90.11%

: 352524-58-4
2-[(5R)-(2-oxo-5-oxazolidinyl)-methyl]-1H-isoindole-1,3(2H)-dione

: 513068-89-8
4-(2-fluoro-4-bromophenyl)morpholine

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
With copper(l) iodide; N,N-dimethyl-ethanamine; potassium carbonate In dichloromethane at 110℃; for 20h; Reagent/catalyst; Solvent; Temperature;	92.8%
With copper(l) iodide; (S,S)-1,2-diaminocyclohexane; potassium carbonate In 1,4-dioxane at 110℃; for 20h; Goldberg Reaction; Inert atmosphere;	76%

: (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

: 1074-82-4
potassium phtalimide

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
at 140 - 145℃; for 2h;	92%
In N,N-dimethyl-formamide for 5h; Reflux;	62%
In N,N-dimethyl-formamide for 5h; Heating / reflux;

: 1074-82-4
potassium phtalimide

: 174649-09-3
(R)-methyl methanesulfonate

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 3h;	87.7%
In N,N-dimethyl-formamide at 120℃; for 2h;
In N,N-dimethyl-formamide at 120℃; for 2h;	27 g

: 1373348-82-3
(S)-3-Chloro-1-(1,3-dioxoisoindolin-2-yl)propan-2-yl-3-fluoro-4-morpholinophenylcarbamate

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 8h;	86%

: 212325-40-1
methyl (3-fluoro-4-morpholinophenyl)carbamate

: 161596-47-0
(S)-N-glycidylphthalimide

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
With lithium tert-butoxide In N,N-dimethyl-formamide at 25 - 85℃; Temperature; Solvent; Reagent/catalyst;	85%
With lithium tert-butoxide In ethyl acetate at 25 - 75℃; Solvent; Temperature; Reagent/catalyst;	70%

: 168828-81-7, 1027135-00-7
benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate

: 161596-47-0
(S)-N-glycidylphthalimide

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Stage #1: benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate With lithium tert-butoxide In tetrahydrofuran; N,N-dimethyl-formamide at 5℃; for 0.5h; Inert atmosphere; Stage #2: (S)-N-glycidylphthalimide In tetrahydrofuran; N,N-dimethyl-formamide at 5 - 20℃; for 24h; Reagent/catalyst; Temperature; Inert atmosphere;	84%

: 51594-55-9
(R)-(-)-epichlorohydrin

: 1074-82-4
potassium phtalimide

: 79-22-1
methyl chloroformate

: 93246-53-8
3-fluoro-4-(morpholinyl)aniline

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Stage #1: (R)-(-)-epichlorohydrin; 3-fluoro-4-(morpholinyl)aniline In butan-1-ol at 20℃; Cooling; Stage #2: methyl chloroformate With sodium hydrogencarbonate In butan-1-ol at 0 - 5℃; Stage #3: potassium phtalimide In N,N-dimethyl-formamide at 95 - 100℃; for 3h;	83%

...Expand

: C21H22FN3O4

: 530-62-1
1,1'-carbonyldiimidazole

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
With dmap In acetonitrile at 80℃; for 1.5h; Inert atmosphere;	70.51%

: 874340-08-6
N-[3-phthalimido-2-(R)-hydroxypropyl]-3-fluoro-4-(4-morpholinyl)aniline

: 530-62-1
1,1'-carbonyldiimidazole

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 20h;
In dichloromethane

: 136918-14-4
phthalimide

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / isopropyl alcohol / 5 h / Reflux 2: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 3: potassium carbonate / dichloromethane / 20 °C 4: potassium carbonate / acetone / 8 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: methylamine / isopropyl alcohol / 5 h / 60 °C 1.2: 10 - 30 °C 2.1: lithium tert-butoxide / N,N-dimethyl-formamide / 25 - 85 °C View Scheme
Multi-step reaction with 3 steps 1: methylamine / isopropyl alcohol / 5 h / 60 °C 2: sodium methylate / methanol / 10 - 30 °C 3: lithium tert-butoxide / ethyl acetate / 25 - 75 °C View Scheme

: 1373348-79-8
(S)-3-chloro-1-(1,3-dioxoisoindolin-2-yl)propan-2-yl chloroformate

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / dichloromethane / 20 °C 2: potassium carbonate / acetone / 8 h / 20 °C View Scheme

: 148857-42-5
2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere 2: potassium carbonate / dichloromethane / 20 °C 3: potassium carbonate / acetone / 8 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 10 - 30 °C 2: lithium tert-butoxide / ethyl acetate / 25 - 75 °C View Scheme

: 868405-66-7
N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholin-4-yl)aniline

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide 2: dichloromethane View Scheme
Multi-step reaction with 5 steps 1: 1,1'-carbonyldiimidazole / dichloromethane / 24 h / 20 - 30 °C 2: N,N-dimethyl-formamide / 120 °C 3: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C 4: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Cooling with ice 5: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 5 steps 1: dichloromethane / 24 h / 25 - 30 °C 2: N,N-dimethyl-formamide / 120 °C 3: sodium t-butanolate; water / tetrahydrofuran / 0.5 h / 0 - 15 °C 4: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C 5: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: dichloromethane / 20 h / 20 °C 2: N,N-dimethyl-formamide / 5 h / Reflux View Scheme

: 93246-53-8
3-fluoro-4-(morpholinyl)aniline

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol 2: N,N-dimethyl-formamide 3: dichloromethane View Scheme
Multi-step reaction with 6 steps 1: tert-butyl alcohol / 16 h / Reflux 2: 1,1'-carbonyldiimidazole / dichloromethane / 24 h / 20 - 30 °C 3: N,N-dimethyl-formamide / 120 °C 4: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C 5: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Cooling with ice 6: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate / water; toluene / 1 h / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -80 - -78 °C / Inert atmosphere 2.2: 20 °C / Cooling 3.1: triethylamine / dichloromethane / 45 °C 4.1: N,N-dimethyl-formamide / 3 h / 80 °C View Scheme

: 93246-53-8
3-fluoro-4-(morpholinyl)aniline

: 161596-47-0
(S)-N-glycidylphthalimide

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide 2: dichloromethane View Scheme
Multi-step reaction with 2 steps 1: ethanol / 16 h / 60 °C / Inert atmosphere 2: dmap / acetonitrile / 1.5 h / 80 °C / Inert atmosphere View Scheme

: 369-34-6
3,4-difluoronitrobenzene

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: triethylamine / acetonitrile / 6 h / 40 - 50 °C / Reflux 2: hydrogen / Raney nickel / methanol / 8 h / 45 - 50 °C / 2942.29 Torr / Autoclave 3: tert-butyl alcohol / 16 h / Reflux 4: 1,1'-carbonyldiimidazole / dichloromethane / 24 h / 20 - 30 °C 5: N,N-dimethyl-formamide / 120 °C 6: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C 7: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Cooling with ice 8: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 6 steps 1.1: triethylamine / dichloromethane / 4 h / 10 - 20 °C 2.1: hydrogen / methanol / 10 h / 20 °C / 3750.38 Torr / Inert atmosphere; Autoclave 3.1: sodium hydrogencarbonate / water; toluene / 1 h / 0 - 20 °C 4.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -80 - -78 °C / Inert atmosphere 4.2: 20 °C / Cooling 5.1: triethylamine / dichloromethane / 45 °C 6.1: N,N-dimethyl-formamide / 3 h / 80 °C View Scheme
Multi-step reaction with 8 steps 1: triethylamine / acetonitrile / 6 h / 40 °C / Reflux 2: hydrogen / methanol / 8 h / 45 - 50 °C / 3000.3 Torr / Autoclave; Inert atmosphere 3: tert-butyl alcohol / 16 h / Reflux 4: dichloromethane / 24 h / 25 - 30 °C 5: N,N-dimethyl-formamide / 120 °C 6: sodium t-butanolate; water / tetrahydrofuran / 0.5 h / 0 - 15 °C 7: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C 8: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / ethyl acetate / 25 - 80 °C 2.1: 5%-palladium/activated carbon; hydrogen / methanol / 22 - 35 °C / 225.02 - 1500.15 Torr 3.1: isopropyl alcohol / 28 - 88 °C 3.2: 35 - 38 °C View Scheme
Multi-step reaction with 4 steps 1.1: triethylamine / ethyl acetate / 24 h / 20 °C 2.1: palladium 10% on activated carbon; ammonium formate / acetone / 8 h / 50 °C 3.1: sodium hydrogencarbonate / acetone; water / 0 - 20 °C 4.1: lithium tert-butoxide / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h / 5 °C / Inert atmosphere 4.2: 24 h / 5 - 20 °C / Inert atmosphere View Scheme

: 2689-39-6
3-fluoro-4-(4-morpholinyl)nitrobenzene

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: hydrogen / Raney nickel / methanol / 8 h / 45 - 50 °C / 2942.29 Torr / Autoclave 2: tert-butyl alcohol / 16 h / Reflux 3: 1,1'-carbonyldiimidazole / dichloromethane / 24 h / 20 - 30 °C 4: N,N-dimethyl-formamide / 120 °C 5: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C 6: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Cooling with ice 7: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 5 steps 1.1: hydrogen / methanol / 10 h / 20 °C / 3750.38 Torr / Inert atmosphere; Autoclave 2.1: sodium hydrogencarbonate / water; toluene / 1 h / 0 - 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -80 - -78 °C / Inert atmosphere 3.2: 20 °C / Cooling 4.1: triethylamine / dichloromethane / 45 °C 5.1: N,N-dimethyl-formamide / 3 h / 80 °C View Scheme
Multi-step reaction with 7 steps 1: hydrogen / methanol / 8 h / 45 - 50 °C / 3000.3 Torr / Autoclave; Inert atmosphere 2: tert-butyl alcohol / 16 h / Reflux 3: dichloromethane / 24 h / 25 - 30 °C 4: N,N-dimethyl-formamide / 120 °C 5: sodium t-butanolate; water / tetrahydrofuran / 0.5 h / 0 - 15 °C 6: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C 7: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1.1: 5%-palladium/activated carbon; hydrogen / methanol / 22 - 35 °C / 225.02 - 1500.15 Torr 2.1: isopropyl alcohol / 28 - 88 °C 2.2: 35 - 38 °C View Scheme
Multi-step reaction with 3 steps 1.1: palladium 10% on activated carbon; ammonium formate / acetone / 8 h / 50 °C 2.1: sodium hydrogencarbonate / acetone; water / 0 - 20 °C 3.1: lithium tert-butoxide / N,N-dimethyl-formamide; tetrahydrofuran / 0.5 h / 5 °C / Inert atmosphere 3.2: 24 h / 5 - 20 °C / Inert atmosphere View Scheme

: 168828-82-8
(R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Cooling with ice 2: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 45 °C 2: N,N-dimethyl-formamide / 3 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C 2: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme

: (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 120 °C 2: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C 3: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Cooling with ice 4: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 120 °C 2: sodium t-butanolate; water / tetrahydrofuran / 0.5 h / 0 - 15 °C 3: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C 4: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme

: 496031-56-2
(R)-(3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl acetate

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: water; sodium t-butanolate / tetrahydrofuran / 0.5 h / 0 - 15 °C 2: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Cooling with ice 3: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme
Multi-step reaction with 3 steps 1: sodium t-butanolate; water / tetrahydrofuran / 0.5 h / 0 - 15 °C 2: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C 3: N,N-dimethyl-formamide / 2 h / 120 °C View Scheme

: 168828-81-7, 1027135-00-7
benzyl 3-fluoro-4-(4-morpholinyl)phenylcarbamate

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -80 - -78 °C / Inert atmosphere 1.2: 20 °C / Cooling 2.1: triethylamine / dichloromethane / 45 °C 3.1: N,N-dimethyl-formamide / 3 h / 80 °C View Scheme

: 51594-55-9
(R)-(-)-epichlorohydrin

: 1074-82-4
potassium phtalimide

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 93246-53-8
3-fluoro-4-(morpholinyl)aniline

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Stage #1: (R)-(-)-epichlorohydrin; 3-fluoro-4-(morpholinyl)aniline In isopropyl alcohol at 28 - 88℃; Stage #2: N,N-dimethyl-formamide at 35 - 38℃; Stage #3: potassium phtalimide Further stages;	234 g

...Expand

: 565176-83-2
N-ethoxycarbonyl-3-fluoro-4-morpholinyl aniline

: 161596-47-0
(S)-N-glycidylphthalimide

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
With triethylamine at 90 - 95℃; for 6h; Reagent/catalyst; Concentration;	40 g

: 212325-40-1
methyl (3-fluoro-4-morpholinophenyl)carbamate

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1.17 h / -10 °C 1.2: 4.67 h / -10 - 55 °C 2.1: 2 h / 140 - 145 °C View Scheme

: 1074-82-4
potassium phtalimide

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 3 h / 80 °C 2: sodium azide; (Dichloroiodo)benzene / ethyl acetate / 12 h / 0 - 80 °C / Inert atmosphere 3: potassium carbonate; N,N-dimethyl-ethanamine; copper(l) iodide / dichloromethane / 20 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 5 h / 70 °C 2: sodium azide; (Dichloroiodo)benzene / ethyl acetate / 12 h / 0 - 80 °C / Inert atmosphere 3: potassium carbonate; N,N-dimethyl-ethanamine; copper(l) iodide / dichloromethane / 20 h / 110 °C View Scheme

: C12H13NO4

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide; (Dichloroiodo)benzene / ethyl acetate / 12 h / 0 - 80 °C / Inert atmosphere 2: potassium carbonate; N,N-dimethyl-ethanamine; copper(l) iodide / dichloromethane / 20 h / 110 °C View Scheme

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: 168828-90-8
(S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol for 4h; Solvent; Reflux;	95.4%
With hydrazine hydrate In methanol for 1h; Reflux;	90%
With hydrazine hydrate In methanol for 1h; Reflux;	71%

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: 108-24-7
acetic anhydride

: 165800-03-3
linezolid

Conditions

Conditions	Yield
Stage #1: 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione With hydrazine In methanol; water at 60℃; for 1h; Stage #2: acetic anhydride With triethylamine at 0 - 20℃; for 2h;	89.1%
Stage #1: 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione With hydrazine hydrate In methanol at 30 - 70℃; Stage #2: acetic anhydride at 10 - 30℃; Concentration;	145 g
Stage #1: 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione With hydrazine hydrate In methanol for 1h; Reflux; Stage #2: acetic anhydride With triethylamine at 10 - 30℃; for 1h;	9 g
Stage #1: 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione With hydrazine hydrate In methanol for 2h; Reflux; Stage #2: acetic anhydride In dichloromethane at 0 - 10℃;

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: 74-89-5
methylamine

: N-[[3-(3-fluoro-4-morphol-4-ylphenyl)-2-oxazolone-5-yl]methyl]-2-methylaminobenzamide

Conditions

Conditions	Yield
In water; acetone for 6h; Reagent/catalyst; Solvent; Reflux;	66.39%

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: 165800-03-3
linezolid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol / 1 h / Reflux 2: toluene / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol / 1 h / Reflux 2: triethylamine / dichloromethane / 1 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol / 1 h / Reflux 2: ethyl acetate / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol / 1 h / Reflux 2: ethyl acetate / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 4 h / Reflux 2: triethylamine / ethyl acetate / 2 h / 20 °C View Scheme

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: (S)-5-chloro-N-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]thiophen-2-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol 2: triethylamine / toluene / 12 h / 20 - 45 °C View Scheme

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: 1390617-34-1
(S)-N-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol 2: triethylamine / toluene / 12 h / 20 - 45 °C View Scheme

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: 1390617-35-2
4-amino-5-(ethylsulfonyl)-N-(S)-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-2-methoxybenzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / methanol 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2.2: 4 h / 0 - 20 °C View Scheme

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / methanol 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2.2: 4 h / 0 - 20 °C View Scheme

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: 1390617-37-4
5-(aminosulfonyl)-N-(S)-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-2-methoxy benzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / methanol 2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 0.5 h / 0 - 20 °C 2.2: 4 h / 0 - 20 °C View Scheme

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: 1390617-32-9
(S)-N-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]-3,4-dimethoxybenzamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol 2: triethylamine / toluene / 12 h / 20 - 45 °C View Scheme

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

: 1390617-33-0
2-benzyl-(S)-N-[[3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxooxazolidin-5-yl]methyl]acrylamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol 2: triethylamine / toluene / 12 h / 20 - 45 °C View Scheme

: 168828-89-5
2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol 2: triethylamine / toluene / 12 h / 20 - 45 °C View Scheme

2-[[(5S)-3-(3-Fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]isoindoline-1,3-dione Specification

The 1H-Isoindole-1,3(2H)-dione,2-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- with CAS registry number of 168828-89-5 is also known as (S)-N-[[3-[3-Fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5- oxazolidinyl]methyl]phthalimide. The systematic name is 2-[[(5S)-3-(3-Fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]isoindoline-1,3-dione. In addition, the formula is C₂₂H₂₀FN₃O₅ and the molecular weight is 425.41.

Physical properties about 1H-Isoindole-1,3(2H)-dione,2-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]- are: (1)ACD/LogP: 2.14; (2)ACD/LogD (pH 5.5): 1.713; (3)ACD/LogD (pH 7.4): 2.133; (4)ACD/BCF (pH 5.5): 9.312; (5)ACD/BCF (pH 7.4): 24.491; (6)ACD/KOC (pH 5.5): 129.807; (7)ACD/KOC (pH 7.4): 341.396; (8)#H bond acceptors: 8 ; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.635; (11)Molar Refractivity: 105.719 cm³; (12)Molar Volume: 295.229 cm³; (13)Surface Tension: 61.456 dyne/cm; (14)Density: 1.441 g/cm³; (15)Flash Point: 328.238 °C; (16)Enthalpy of Vaporization: 91.78 kJ/mol; (17)Boiling Point: 619.13 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
1. SMILES: c1ccc2c(c1)C(=O)N(C2=O)C[C@H]3CN(C(=O)O3)c4ccc(c(c4)F)N5CCOCC5
2. InChI: InChI=1/C22H20FN3O5/c23-18-11-14(5-6-19(18)24-7-9-30-10-8-24)25-12-15(31-22(25)29)13-26-20(27)16-3-1-2-4-17(16)21(26)28/h1-6,11,15H,7-10,12-13H2/t15-/m1/s1
3. InChIKey: FKZUTWSVQLXKQE-OAHLLOKOBL
4. Std. InChI: InChI=1S/C22H20FN3O5/c23-18-11-14(5-6-19(18)24-7-9-30-10-8-24)25-12-15(31-22(25)29)13-26-20(27)16-3-1-2-4-17(16)21(26)28/h1-6,11,15H,7-10,12-13H2/t15-/m1/s1
5. Std. InChIKey: FKZUTWSVQLXKQE-OAHLLOKOSA-N

Product Name

DeacetaMide Linezolid PhthaliMide

Synthetic route

2-[[(5S)-3-(3-Fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]isoindoline-1,3-dione Specification

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