(S)-5-(Aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one supplier

Name
(S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine
EINECS 1806241-263-5
CAS No. 168828-90-8
Article Data51
CAS DataBase
Density 1.32 g/cm³
Solubility
Melting Point
Formula C₁₄H₁₈FN₃O₃
Boiling Point 480.02 °C at 760 mmHg
Molecular Weight 295.314
Flash Point 244.107 °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]amine;
PSA 68.03000
LogP 1.77650

Synthetic route

: 168828-84-0
(R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one

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

Conditions

Conditions	Yield
With water; triphenylphosphine In tetrahydrofuran at 70℃;	100%
With hydrogen In methanol at 40 - 60℃; under 3750.38 Torr; for 3h; Temperature; Pressure; Reagent/catalyst; Autoclave;	98%
With palladium on activated charcoal; hydrogen; acetic acid In methanol for 2h;	81%

: 165800-03-3
linezolid

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

Conditions

Conditions	Yield
With hydrogenchloride In methanol Reflux;	99%
With pyridine; hydroxylamine hydrochloride In ethanol for 48h; Sealed tube;

: 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%

: 1236077-61-4
(S)-5-((benzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

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

Conditions

Conditions	Yield
With hydrogen; acetic acid; 5% Pd(II)/C(eggshell) In methanol at 40℃; under 7355.72 - 8826.87 Torr;	95%
With ammonium formate; palladium 10% on activated carbon In methanol at 65℃; for 8h;

: 565176-85-4
(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholino phenyl)-isooxazol-2-one

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

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In acetone at 25℃; under 37503.8 Torr; for 5h; Product distribution / selectivity;	93%
With hydrogen; palladium 10% on activated carbon In acetone at 25℃; under 37503.8 Torr; for 5h; Product distribution / selectivity;	93%

: 1215006-07-7
(S)-5-((allylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

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

Conditions

Conditions	Yield
Stage #1: (S)-5-((allylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one With 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine In ethanol at 35℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water pH=1; Stage #3: With sodium hydroxide In water pH=10;	81%

: (R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-iodobenzenesulfonate

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

Conditions

Conditions	Yield
With ammonia In methanol at 70℃; under 3750.38 Torr; for 20h;	67.7%

: (R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-bromobenzenesulfonate

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

Conditions

Conditions	Yield
With ammonia In methanol at 80℃; under 4500.45 Torr; for 20h;	67.6%

: (R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-fluorobenzenesulfonate

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

Conditions

Conditions	Yield
With ammonia In methanol at 75℃; under 5250.53 Torr; for 20h;	65.8%

: (R)-[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-5-oxazolidinyl]methyl p-chlorobenzenesulfonate

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

Conditions

Conditions	Yield
With ammonia In methanol at 90℃; under 4500.45 Torr; for 20h;	65.5%

: 198410-26-3
4-Nitro-benzenesulfonic acid (R)-3-(3-fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester

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

Conditions

Conditions	Yield
With ammonia In methanol

: 3-(3-fluoro-4-morpholin-4-yl-phenylamino)-propan-1-ol

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

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: aq. NaHCO3 / acetone 2.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C 3.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 3.2: NaBH4 / methanol 3.3: 86 percent / CuSO4 / methanol 4.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 5.1: Et3N / CH2Cl2 / 4 h / 0 °C 6.1: NaN3 / dimethylformamide / 75 °C 7.1: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr View Scheme

Yield

Multi-step reaction with 7 steps
1.1: aq. NaHCO3 / acetone
2.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
3.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
3.2: NaBH4 / methanol
3.3: 86 percent / CuSO4 / methanol
4.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
5.1: Et3N / CH2Cl2 / 4 h / 0 °C
6.1: NaN3 / dimethylformamide / 75 °C
7.1: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr
View Scheme

: 912552-55-7
(3-fluoro-4-morpholin-4-yl-phenyl)-(3-oxo-propyl)-carbamic acid benzyl ester

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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 1.2: NaBH4 / methanol 1.3: 86 percent / CuSO4 / methanol 2.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 3.1: Et3N / CH2Cl2 / 4 h / 0 °C 4.1: NaN3 / dimethylformamide / 75 °C 5.1: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr View Scheme

: 912552-54-6
(3-fluoro-4-morpholin-4-yl-phenyl)-(3-hydroxy-propyl)-carbamic acid benzyl ester

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

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C 2.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 2.2: NaBH4 / methanol 2.3: 86 percent / CuSO4 / methanol 3.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 4.1: Et3N / CH2Cl2 / 4 h / 0 °C 5.1: NaN3 / dimethylformamide / 75 °C 6.1: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr View Scheme

Yield

Multi-step reaction with 6 steps
1.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C
2.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C
2.2: NaBH4 / methanol
2.3: 86 percent / CuSO4 / methanol
3.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C
4.1: Et3N / CH2Cl2 / 4 h / 0 °C
5.1: NaN3 / dimethylformamide / 75 °C
6.1: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr
View Scheme

: 912552-56-8
((S)-2,3-Dihydroxy-propyl)-(3-fluoro-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 2: Et3N / CH2Cl2 / 4 h / 0 °C 3: NaN3 / dimethylformamide / 75 °C 4: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: NaI; Na2CO3 / dimethylformamide / 65 °C 2.1: aq. NaHCO3 / acetone 3.1: 95 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - -60 °C 4.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C 4.2: NaBH4 / methanol 4.3: 86 percent / CuSO4 / methanol 5.1: 96 percent / sodium hydride / tetrahydrofuran / 0 °C 6.1: Et3N / CH2Cl2 / 4 h / 0 °C 7.1: NaN3 / dimethylformamide / 75 °C 8.1: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr View Scheme
Multi-step reaction with 4 steps 1.1: NaHCO3 2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 2.2: hexane; tetrahydrofuran / -78 - 20 °C 3.1: Et3N 4.1: NH3 / methanol View Scheme
Multi-step reaction with 4 steps 1: Et3N / tetrahydrofuran / 2 h / 20 °C 2: sodium azide / dimethylformamide / 6 h / 65 °C 3: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 4 h / 0 °C 2: NaN3 / dimethylformamide / 75 °C 3: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr View Scheme
Multi-step reaction with 2 steps 1: Et3N 2: NH3 / methanol View Scheme
Multi-step reaction with 3 steps 1: Et3N / tetrahydrofuran / 2 h / 20 °C 2: sodium azide / dimethylformamide / 6 h / 65 °C 3: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaN3 / dimethylformamide / 75 °C 2: hydrogen / Pd/C / ethyl acetate / 12 h / 760 Torr View Scheme
Multi-step reaction with 2 steps 1: sodium azide / dimethylformamide / 6 h / 65 °C 2: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: sodium azide / dimethylformamide / 16 h / 75 °C 2: H2 / Pd/C / ethyl acetate View Scheme

: 369-34-6
3,4-difluoronitrobenzene

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

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: N,N-diisopropylethylamine 2.1: ammonium formate / 10 percent Pd/C / methanol; tetrahydrofuran 3.1: NaHCO3 4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 4.2: hexane; tetrahydrofuran / -78 - 20 °C 5.1: Et3N 6.1: NH3 / methanol View Scheme
Multi-step reaction with 6 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 4: sodium azide / dimethylformamide / 6 h / 65 °C 5: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C View Scheme
Multi-step reaction with 7 steps 1: 98 percent / N,N-diisopropylethylamine / ethyl acetate 2: ammonium formate / 10percent Pd/C 3: 70 percent / sodium bicarbonate / acetone; H2O 4: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h 5: 35.423 g / triethylamine / CH2Cl2 / 20 h 6: sodium azide / dimethylformamide / 16 h / 75 °C 7: H2 / Pd/C / ethyl acetate View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: ammonium formate / 10 percent Pd/C / methanol; tetrahydrofuran 2.1: NaHCO3 3.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 3.2: hexane; tetrahydrofuran / -78 - 20 °C 4.1: Et3N 5.1: NH3 / methanol View Scheme
Multi-step reaction with 5 steps 1: H2 / PtO2 / methanol / 3 h / 20 °C / 1471.02 Torr 2: Et3N / tetrahydrofuran / 2 h / 20 °C 3: sodium azide / dimethylformamide / 6 h / 65 °C 4: triphenylphosphine; H2O / tetrahydrofuran / 11 h / 40 °C View Scheme
Multi-step reaction with 6 steps 1: ammonium formate / 10percent Pd/C 2: 70 percent / sodium bicarbonate / acetone; H2O 3: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h 4: 35.423 g / triethylamine / CH2Cl2 / 20 h 5: sodium azide / dimethylformamide / 16 h / 75 °C 6: H2 / Pd/C / ethyl acetate View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 1.2: hexane; tetrahydrofuran / -78 - 20 °C 2.1: Et3N 3.1: NH3 / methanol View Scheme
Multi-step reaction with 4 steps 1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h 2: 35.423 g / triethylamine / CH2Cl2 / 20 h 3: sodium azide / dimethylformamide / 16 h / 75 °C 4: H2 / Pd/C / ethyl acetate View Scheme
Multi-step reaction with 4 steps 1.1: butan-1-ol; n-butyllithium / hexane; tetrahydrofuran / -15 - 30 °C / Inert atmosphere 1.2: -10 - 15 °C 2.1: triethylamine / dichloromethane / 20 - 30 °C 3.1: sodium azide / N,N-dimethyl-formamide / 60 °C / Reflux 4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 15 - 20 °C / Autoclave View Scheme

: 1027321-41-0
(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-5-({[(1S)-1-phenylethyl]amino}methyl)-1,3-oxazolidin-2-one

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

Conditions

Conditions	Yield
With palladium 10% on activated carbon; ammonium formate In methanol at 20℃; Inert atmosphere;

: 168828-83-9
(R)-[N-3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl 4-methylbenzenesulfonate

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 h / 70 °C 2: ammonium formate / palladium 10% on activated carbon / methanol / 8 h / 65 °C View Scheme
With sodium diformamide; N,N-dimethyl-formamide at 85℃; for 2h; Inert atmosphere;	18.87 g

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

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 1.3: 0.5 h / 20 °C 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: 5 h / 70 °C 4.1: ammonium formate / palladium 10% on activated carbon / methanol / 8 h / 65 °C View Scheme

: 350-31-2
1-chloro-2-fluoro-4-nitrobenzene

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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: Neat (no solvent) 2.1: ammonium formate / palladium 10% on activated carbon / tetrahydrofuran; methanol / 20 °C / Inert atmosphere; cooling with ice 3.1: toluene / -20 °C / Inert atmosphere; Reflux 4.1: Tributylphosphine oxide; lithium bromide / o-xylene / 1 h / Reflux 5.1: hydrogenchloride; water / 0.25 h / 20 °C 5.2: pH 8 - 9 View Scheme
Multi-step reaction with 5 steps 1.1: Neat (no solvent) 2.1: ammonium formate / palladium 10% on activated carbon / tetrahydrofuran; methanol / 20 °C / Inert atmosphere; cooling with ice 3.1: toluene / -20 °C / Inert atmosphere; Reflux 4.1: Tributylphosphine oxide; lithium bromide / toluene / 1 h / Inert atmosphere; Reflux 5.1: hydrogenchloride / dichloromethane; water / 1 h / 20 °C 5.2: pH 7 / cooling with ice View Scheme

Yield

Multi-step reaction with 5 steps
1.1: Neat (no solvent)
2.1: ammonium formate / palladium 10% on activated carbon / tetrahydrofuran; methanol / 20 °C / Inert atmosphere; cooling with ice
3.1: toluene / -20 °C / Inert atmosphere; Reflux
4.1: Tributylphosphine oxide; lithium bromide / o-xylene / 1 h / Reflux
5.1: hydrogenchloride; water / 0.25 h / 20 °C
5.2: pH 8 - 9
View Scheme

Multi-step reaction with 5 steps
1.1: Neat (no solvent)
2.1: ammonium formate / palladium 10% on activated carbon / tetrahydrofuran; methanol / 20 °C / Inert atmosphere; cooling with ice
3.1: toluene / -20 °C / Inert atmosphere; Reflux
4.1: Tributylphosphine oxide; lithium bromide / toluene / 1 h / Inert atmosphere; Reflux
5.1: hydrogenchloride / dichloromethane; water / 1 h / 20 °C
5.2: pH 7 / cooling with ice
View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Tributylphosphine oxide; lithium bromide / o-xylene / 1 h / Reflux 2.1: hydrogenchloride; water / 0.25 h / 20 °C 2.2: pH 8 - 9 View Scheme
Multi-step reaction with 2 steps 1.1: Tributylphosphine oxide; lithium bromide / toluene / 1 h / Inert atmosphere; Reflux 2.1: hydrogenchloride / dichloromethane; water / 1 h / 20 °C 2.2: pH 7 / cooling with ice View Scheme
Multi-step reaction with 2 steps 1: lithium bromide; Tributylphosphine oxide / toluene / 0.25 h / Inert atmosphere; Reflux 2: hydrogenchloride; water / dichloromethane / 0.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: magnesium halide / 4 h / 80 °C 2.1: sodium azide / N,N-dimethyl-formamide / 3 h / 85 °C 2.2: 20 h / 20 °C / 760.05 Torr View Scheme
Multi-step reaction with 3 steps 1: MgI2 etherate / neat (no solvent) / 20 - 65 °C 2: sodium azide / N,N-dimethyl-formamide / 12 h / 85 °C 3: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 12 h View Scheme

: 100-00-5
4-chlorobenzonitrile

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

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: fluorine; sulfuric acid 2.1: Neat (no solvent) 3.1: ammonium formate / palladium 10% on activated carbon / tetrahydrofuran; methanol / 20 °C / Inert atmosphere; cooling with ice 4.1: toluene / -20 °C / Inert atmosphere; Reflux 5.1: Tributylphosphine oxide; lithium bromide / o-xylene / 1 h / Reflux 6.1: hydrogenchloride; water / 0.25 h / 20 °C 6.2: pH 8 - 9 View Scheme
Multi-step reaction with 6 steps 1.1: fluorine; sulfuric acid 2.1: Neat (no solvent) 3.1: ammonium formate / palladium 10% on activated carbon / tetrahydrofuran; methanol / 20 °C / Inert atmosphere; cooling with ice 4.1: toluene / -20 °C / Inert atmosphere; Reflux 5.1: Tributylphosphine oxide; lithium bromide / toluene / 1 h / Inert atmosphere; Reflux 6.1: hydrogenchloride / dichloromethane; water / 1 h / 20 °C 6.2: pH 7 / cooling with ice View Scheme

Yield

Multi-step reaction with 6 steps
1.1: fluorine; sulfuric acid
2.1: Neat (no solvent)
3.1: ammonium formate / palladium 10% on activated carbon / tetrahydrofuran; methanol / 20 °C / Inert atmosphere; cooling with ice
4.1: toluene / -20 °C / Inert atmosphere; Reflux
5.1: Tributylphosphine oxide; lithium bromide / o-xylene / 1 h / Reflux
6.1: hydrogenchloride; water / 0.25 h / 20 °C
6.2: pH 8 - 9
View Scheme

Multi-step reaction with 6 steps
1.1: fluorine; sulfuric acid
2.1: Neat (no solvent)
3.1: ammonium formate / palladium 10% on activated carbon / tetrahydrofuran; methanol / 20 °C / Inert atmosphere; cooling with ice
4.1: toluene / -20 °C / Inert atmosphere; Reflux
5.1: Tributylphosphine oxide; lithium bromide / toluene / 1 h / Inert atmosphere; Reflux
6.1: hydrogenchloride / dichloromethane; water / 1 h / 20 °C
6.2: pH 7 / cooling with ice
View Scheme

: 1330034-71-3
(S)-(E,Z)-5-((benzylideneamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

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

Conditions

Conditions	Yield
Stage #1: (S)-(E,Z)-5-((benzylideneamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one With hydrogenchloride; water at 20℃; for 0.25h; Stage #2: With sodium hydroxide In water pH=8 - 9;

: 1345879-82-4
(S)-(E,Z)-5-((4-chlorobenzylideneamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

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

Conditions

Conditions	Yield
Stage #1: (S)-(E,Z)-5-((4-chlorobenzylideneamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one With hydrogenchloride In dichloromethane; water at 20℃; for 1h; Stage #2: With sodium hydroxide In dichloromethane; water pH=7; Product distribution / selectivity; cooling with ice;
With hydrogenchloride; water In dichloromethane at 20℃; for 0.5h;

: C20H21FN2O6S

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

Conditions

Conditions	Yield
Stage #1: C20H21FN2O6S With sodium diformamide In N,N-dimethyl-formamide at 85℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 85℃; for 2.5h; Inert atmosphere; Stage #3: With sodium hydroxide In dichloromethane; water; N,N-dimethyl-formamide at 20℃; Inert atmosphere;
Stage #1: C20H21FN2O6S With sodium diformamide In N,N-dimethyl-formamide at 85℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 85℃; for 2.5h; Inert atmosphere; Stage #3: With sodium hydroxide In dichloromethane; water; N,N-dimethyl-formamide at 20℃; Inert atmosphere;

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

: 183905-31-9
N-[(2S)-2-acetoxy-3-chloropropyl]acetamide

: (R)-1-acetamido-3-((((S)-3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)amino)propan-2-yl acetate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;	97.9%

: 88-14-2
2-furanoic acid

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

: (S)-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)furan-2-carboxamide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12.5h;	95%

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

: 7-methoxy-2-methyl-N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-3-quinolinecarboxamide

Conditions

Conditions	Yield
Stage #1: 7-methoxy-2-methylquinoline-3-carboxylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine In dichloromethane at 20℃; for 12h;	95%

: 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

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

: 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
Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0 - 20℃; for 0.5h; Stage #2: (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine In dichloromethane at 0 - 20℃; for 4h;	93%

: 75-36-5
acetyl chloride

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

: 165800-03-3
linezolid

Conditions

Conditions	Yield
With triethylamine In ethyl acetate at 20℃; for 2h;	92.8%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	85%
With triethylamine In dichloromethane at 20℃; Inert atmosphere;	73 mg
With triethylamine In N,N-dimethyl-formamide at 2℃;	9.8 g

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

: 168828-84-0
(R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one

Conditions

Conditions	Yield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;	92%

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

: 91257-99-7
N′-(2,2-dichloro-1-methylethylidene)-4-methylbenzenesulfonohydrazide

: 1170353-86-2
(R)-3-(3-fluoro-4-morpholinophenyl)-5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol at 0℃; Inert atmosphere;	91%

: 65-85-0
benzoic acid

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

: 1609632-44-1
N-(3-(3-fluoro-4-(morpholin-4-yl)phenyl)-2-oxooxazolidin-5(S)-ylmethyl)amine benzoate

Conditions

Conditions	Yield
In methanol; water; isopropyl alcohol at 80℃;	89.5%

: 64-19-7
acetic acid

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

: (S)-5-(aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one acetate

Conditions

Conditions	Yield
Stage #1: (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine With hydrogen; palladium 10% on activated carbon In ethyl acetate at 50℃; under 608.041 - 912.061 Torr; for 20h; Stage #2: acetic acid Product distribution / selectivity;	89%

: 108-24-7
acetic anhydride

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

: 165800-03-3
linezolid

Conditions

Conditions	Yield
With triethylamine In ethyl acetate at 20 - 40℃; under 608.041 - 912.061 Torr; for 2h; Product distribution / selectivity;	88%
With triethylamine In ethyl acetate at 25℃; for 2h; Product distribution / selectivity;	88%
at 0℃;	88%

: 5222-73-1
3,4-dimethoxy-3-cyclobutene-1,2-dione

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

: 1308299-21-9
(S)-3-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methylamino)-4-methoxycyclobut-3-ene-1,2-dione

Conditions

Conditions	Yield
With triethylamine In methanol at 20℃; pH=7.5;	88%

: 42518-98-9
5-chlorothiophene-2-carbonyl chloride

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

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

Conditions

Conditions	Yield
With triethylamine In toluene at 20 - 45℃; for 12h;	87%

: 107089-76-9
NSC 373853

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

: 1280555-25-0
C22H24FN5O5S

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 6h;	85%

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

: 3535-37-3
3,4-dimethoxybenzoic acid chloride

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

Conditions

Conditions	Yield
With triethylamine In toluene at 20 - 45℃; for 12h;	83%

: 7028-67-3
4-(4-methylsulfanyl-phenyl)-4-oxo-butyric acid

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

: 675609-11-7
(S)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]-4-oxo-4-(4-thiomethyl)phenylbutanamide

Conditions

Conditions	Yield
Stage #1: 4-(4-methylsulfanyl-phenyl)-4-oxo-butyric acid; (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; water at 0 - 20℃; for 24h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 0.25h;	79%

: 75-36-5
acetyl chloride

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

A: (S)-N-acetyl-N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

B: 165800-03-3
linezolid

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;	A 8% B 79%

...Expand

: 39493-62-4
2-oxo-4-hydroxy-6-methyl-cyclohex-3-ene carboxylic acid methyl ester

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

: 1147846-91-0
methyl 4-(((S)-3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methylamino)-6-methyl-2-oxocyclohex-3-enecarboxylate

Conditions

Conditions	Yield
Reflux;	77%

: 1117-71-1
methyl 4-bromocrotonate

: 124-38-9
carbon dioxide

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

: methyl 2-(3-(((S)-3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)-2-oxooxazolidin-4-yl)acetate

Conditions

Conditions	Yield
With caesium carbonate; N,N,N',N'-tetramethylguanidine In N,N-dimethyl-formamide at 20℃; for 30h; Michael Addition; Schlenk technique; Sealed tube;	74%

...Expand

: ethyl furan-2-carboxycyanoimidate

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

: N-[[(5S)-3-[3-fluoro-4-(4-morpholinyl)-phenyl]-2-oxo-5-oxazolidinyl]methyl]furan-2-yl-cyanoamidine

Conditions

Conditions	Yield
In methanol Heating / reflux;	73%

: 79-04-9
chloroacetyl chloride

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

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

Conditions

Conditions	Yield
With triethylamine In toluene at 20 - 45℃; for 12h;	71%
Stage #1: (S)-N-[[3-[3-fluoro-4-[4-morpholinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]amine With triethylamine In dichloromethane for 0.25h; Stage #2: chloroacetyl chloride In dichloromethane at 20℃; for 18h; Cooling with ice;
With potassium carbonate In acetone at 20℃;
With potassium carbonate In acetone at 20℃;

: 349-88-2
4-Fluorobenzenesulfonyl chloride

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

: 1280555-38-5
(R)-[{N-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl}methyl] 4-fluorobenzensulfonamide

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 6h;	70%

: 98-60-2
4-chlorobenzenesulfonyl chloride

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

: 1280555-37-4
(R)-[{N-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl}methyl] 4-chlorobenzensulfonamide

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 6h;	70%

: 98-09-9
benzenesulfonyl chloride

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

: 1280555-36-3
(R)-[{N-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl}methyl] benzensulfonamide

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 6h;	70%

: 98-59-9
p-toluenesulfonyl chloride

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

: 1280555-41-0
(R)-[{N-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl}methyl] 4-methylbenzensulfonamide

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0℃; for 6h;	70%

(S)-5-(Aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one Specification

The CAS registry number of 2-Oxazolidinone, 5-(aminomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-,(5S)- is 168828-90-8. The systematic name is (5S)-5-(aminomethyl)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-1,3-oxazolidin-2-one. In addition, the molecular formula is C₁₄H₁₈FN₃O₃ and the molecular weight is 295.31. What's more, it should be stored in sealed container, and put in a cool and dry place.

Physical properties about 2-Oxazolidinone, 5-(aminomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-,(5S)- are: (1)ACD/LogP: 0.64; (2)ACD/LogD (pH 5.5): -3; (3)ACD/LogD (pH 7.4): -1; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 6; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 68.03 Å²; (12)Index of Refraction: 1.572; (13)Molar Refractivity: 73.614 cm³; (14)Molar Volume: 223.767 cm³; (15)Polarizability: 29.183 ×10^-24cm³; (16)Surface Tension: 50.656 dyne/cm; (17)Density: 1.32 g/cm³; (18)Flash Point: 244.107 °C; (19)Enthalpy of Vaporization: 74.444 kJ/mol; (20)Boiling Point: 480.02 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1O[C@@H](CN)CN1c3cc(F)c(N2CCOCC2)cc3
(2)InChI: InChI=1/C14H18FN3O3/c15-12-7-10(18-9-11(8-16)21-14(18)19)1-2-13(12)17-3-5-20-6-4-17/h1-2,7,11H,3-6,8-9,16H2/t11-/m0/s1
(3)InChIKey: VXIWZOWWQMRVRF-NSHDSACABS

Product Name

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

Synthetic route

(S)-5-(Aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one Specification

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