(R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone supplier

Name
(R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone
EINECS
CAS No. 168828-84-0
Article Data25
CAS DataBase
Density
Solubility
Melting Point 102.5-103.5 °C
Formula C14H16 F N5 O3
Boiling Point
Molecular Weight 321.311
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Oxazolidinone,5-(azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-,(R)-
PSA 91.76000
LogP 1.88056

Synthetic route

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

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

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 85℃;	97.23%
With sodium azide In N,N-dimethyl-formamide at 60℃; Reflux;	95%
With sodium azide In tetrahydrofuran; water for 8h; Reflux;	93%

: 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%

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

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

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 80 - 85℃; for 4h;	90%

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

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

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 85℃; for 12h;	87%
With sodium azide In N,N-dimethyl-formamide at 85℃; for 12h;	86%

: 677726-40-8
(R)-5-azidomethyl-1,3-oxazolidin-2-one

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

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

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate; rac-diaminocyclohexane In 1,4-dioxane at 110℃; for 23h;	84%

: 1373348-81-2
(S)-3-azido-1-chloropropan-2-yl 3-fluoro-4-morpholinophenylcarbamate

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

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 8h;	83%

: 677726-40-8
(R)-5-azidomethyl-1,3-oxazolidin-2-one

: 1250999-09-7
4-(2-fluoro-4-iodophenyl)morpholine

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

Conditions

Conditions	Yield
With trans-1,2-Diaminocyclohexane; potassium carbonate; copper(l) chloride In 1,4-dioxane at 110℃; for 15h; Inert atmosphere; Darkness;	82%
With potassium carbonate; trans-1,2-Diaminocyclohexane; copper(l) chloride In 1,4-dioxane at 110℃; for 15h; Inert atmosphere; Darkness; Sealed vessel;	82%

: 1373348-78-7
(S)-3-azido-1-chloropropan-2-yl chloroformate

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

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

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃;	82%

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

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

Conditions

Conditions	Yield
Stage #1: (R)-3-(3-fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl methanol With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; Stage #2: With sodium azide In N,N-dimethyl-formamide at 80℃; Further stages.;	79%
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 4 h / 0 °C 2: NaN3 / dimethylformamide / 75 °C View Scheme
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 2 h / 20 °C 2: sodium azide / dimethylformamide / 6 h / 65 °C View Scheme

: 1223581-08-5
(R)-N-(3-fluoro-4-morpholinylphenyl)oxiranylmethyl carbamic acid ethyl ester

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

Conditions

Conditions	Yield
With sodium azide; ammonium chloride In methanol; water at 80 - 85℃; for 4h;	76%

: 881012-11-9
3-chloro-2-((phenoxycarbonyl)oxy)propyl azide

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

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

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;

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

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

Conditions

Conditions	Yield
Multi-step reaction with 6 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 View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 4 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 View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 5 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 View Scheme

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

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

Conditions

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

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

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

Conditions

Conditions	Yield
Multi-step reaction with 7 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 View Scheme
Multi-step reaction with 3 steps 1: Et3N / tetrahydrofuran / 2 h / 20 °C 2: sodium azide / dimethylformamide / 6 h / 65 °C View Scheme
Multi-step reaction with 4 steps 1: 70 percent / sodium bicarbonate / acetone; H2O 2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 35 min, 2.) THF, hexane, -78 deg C, 1 h 3: 35.423 g / triethylamine / CH2Cl2 / 20 h 4: sodium azide / dimethylformamide / 16 h / 75 °C View Scheme

: 369-34-6
3,4-difluoronitrobenzene

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

Conditions

Conditions	Yield
Multi-step reaction with 5 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 View Scheme
Multi-step reaction with 6 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 View Scheme
Multi-step reaction with 6 steps 1.1: methanol / 25 - 30 °C 2.1: hydrogen / palladium 10% on activated carbon / methanol / 20 - 30 °C / Autoclave 3.1: sodium carbonate / toluene; acetone / 0 - 5 °C 4.1: butan-1-ol; n-butyllithium / hexane; tetrahydrofuran / -15 - 30 °C / Inert atmosphere 4.2: -10 - 15 °C 5.1: triethylamine / dichloromethane / 20 - 30 °C 6.1: sodium azide / N,N-dimethyl-formamide / 60 °C / Reflux View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 4 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 View Scheme
Multi-step reaction with 5 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 View Scheme
Multi-step reaction with 5 steps 1.1: hydrogen / palladium 10% on activated carbon / methanol / 20 - 30 °C / Autoclave 2.1: sodium carbonate / toluene; acetone / 0 - 5 °C 3.1: butan-1-ol; n-butyllithium / hexane; tetrahydrofuran / -15 - 30 °C / Inert atmosphere 3.2: -10 - 15 °C 4.1: triethylamine / dichloromethane / 20 - 30 °C 5.1: sodium azide / N,N-dimethyl-formamide / 60 °C / Reflux View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: NaBH4 / methanol / 0 °C 2: Et3N 3: NaN3 / dimethylsulfoxide / 80 °C View Scheme

: 905945-96-2
(R)-2-(3-Fluoro-4-morpholin-4-yl-phenylamino)-1-{(4R,5R)-5-[(R)-2-(3-fluoro-4-morpholin-4-yl-phenylamino)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethanol

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

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: CH2Cl2 / Ambient temperature 2: 2N HCl / Ambient temperature 3: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C 4: NaBH4 / methanol / 0 °C 5: Et3N 6: NaN3 / dimethylsulfoxide / 80 °C View Scheme

: 239438-43-8
C28H32F2N4O8

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C 2: NaBH4 / methanol / 0 °C 3: Et3N 4: NaN3 / dimethylsulfoxide / 80 °C View Scheme

: 239438-39-2
C31H36F2N4O8

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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 2N HCl / Ambient temperature 2: lead tetraacetate (LTA) / tetrahydrofuran / 0 °C 3: NaBH4 / methanol / 0 °C 4: Et3N 5: NaN3 / dimethylsulfoxide / 80 °C View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 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 View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 1.3: 0.17 h / 20 °C 2.1: triethylamine / dichloromethane / 18 h / 0 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / -78 °C 1.2: -78 - 20 °C 2.1: triethylamine / dichloromethane 3.1: sodium azide / N,N-dimethyl-formamide / 70 °C View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / -30 - -20 °C 1.2: -30 - 50 °C 2.1: triethylamine / dichloromethane / 0 - 5 °C 3.1: sodium azide / N,N-dimethyl-formamide / 2 h / 25 - 85 °C View Scheme

: 1201594-21-9
C8H10FNO3S

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 2.1: N-iodo-succinimide; trifluoroacetic acid / 14 h / 23 °C / Inert atmosphere 2.2: 23 °C 3.1: trans-1,2-Diaminocyclohexane; potassium carbonate; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness View Scheme
Multi-step reaction with 3 steps 1: sodium t-butanolate / bis(1,5-cyclooctadiene)nickel (0); 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere; Sealed vessel 2: trifluoroacetic acid; N-iodo-succinimide / 14 h / 23 °C / Inert atmosphere; Sealed vessel 3: potassium carbonate / trans-1,2-Diaminocyclohexane; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness; Sealed vessel View Scheme

Yield

Multi-step reaction with 3 steps
1.1: bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere
2.1: N-iodo-succinimide; trifluoroacetic acid / 14 h / 23 °C / Inert atmosphere
2.2: 23 °C
3.1: trans-1,2-Diaminocyclohexane; potassium carbonate; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness
View Scheme

Multi-step reaction with 3 steps
1: sodium t-butanolate / bis(1,5-cyclooctadiene)nickel (0); 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere; Sealed vessel
2: trifluoroacetic acid; N-iodo-succinimide / 14 h / 23 °C / Inert atmosphere; Sealed vessel
3: potassium carbonate / trans-1,2-Diaminocyclohexane; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness; Sealed vessel
View Scheme

: 66950-63-8
phenyl N,N-dimethylsulfamate

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Inert atmosphere 2.1: bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 3.1: N-iodo-succinimide; trifluoroacetic acid / 14 h / 23 °C / Inert atmosphere 3.2: 23 °C 4.1: trans-1,2-Diaminocyclohexane; potassium carbonate; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness View Scheme

Yield

Multi-step reaction with 4 steps
1.1: Inert atmosphere
2.1: bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere
3.1: N-iodo-succinimide; trifluoroacetic acid / 14 h / 23 °C / Inert atmosphere
3.2: 23 °C
4.1: trans-1,2-Diaminocyclohexane; potassium carbonate; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness
View Scheme

: N-(2-fluorophenyl)-morpholine

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-iodo-succinimide; trifluoroacetic acid / 14 h / 23 °C / Inert atmosphere 1.2: 23 °C 2.1: trans-1,2-Diaminocyclohexane; potassium carbonate; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness View Scheme
Multi-step reaction with 2 steps 1: trifluoroacetic acid; N-iodo-succinimide / 14 h / 23 °C / Inert atmosphere; Sealed vessel 2: potassium carbonate / trans-1,2-Diaminocyclohexane; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness; Sealed vessel View Scheme

: 108-95-2
phenol

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

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: Inert atmosphere 2.1: Inert atmosphere 3.1: bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 4.1: N-iodo-succinimide; trifluoroacetic acid / 14 h / 23 °C / Inert atmosphere 4.2: 23 °C 5.1: trans-1,2-Diaminocyclohexane; potassium carbonate; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness View Scheme

Yield

Multi-step reaction with 5 steps
1.1: Inert atmosphere
2.1: Inert atmosphere
3.1: bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere
4.1: N-iodo-succinimide; trifluoroacetic acid / 14 h / 23 °C / Inert atmosphere
4.2: 23 °C
5.1: trans-1,2-Diaminocyclohexane; potassium carbonate; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness
View Scheme

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

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

Conditions

Conditions	Yield
Multi-step reaction with 3 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: sodium azide / N,N-dimethyl-formamide / 4 h / 80 - 85 °C View Scheme

: 367-12-4
2-fluorophenol

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydride / 1,2-dimethoxyethane; mineral oil / 15 h / 23 °C / Inert atmosphere 2: sodium t-butanolate / bis(1,5-cyclooctadiene)nickel (0); 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 3: trifluoroacetic acid; N-iodo-succinimide / 14 h / 23 °C / Inert atmosphere; Sealed vessel 4: potassium carbonate / trans-1,2-Diaminocyclohexane; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness; Sealed vessel View Scheme

Yield

Multi-step reaction with 4 steps
1: sodium hydride / 1,2-dimethoxyethane; mineral oil / 15 h / 23 °C / Inert atmosphere
2: sodium t-butanolate / bis(1,5-cyclooctadiene)nickel (0); 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere
3: trifluoroacetic acid; N-iodo-succinimide / 14 h / 23 °C / Inert atmosphere; Sealed vessel
4: potassium carbonate / trans-1,2-Diaminocyclohexane; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness; Sealed vessel
View Scheme

: 459408-52-7
2-fluorophenyl diethylcarbamate

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium t-butanolate / bis(1,5-cyclooctadiene)nickel (0); 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere 2: trifluoroacetic acid; N-iodo-succinimide / 14 h / 23 °C / Inert atmosphere; Sealed vessel 3: potassium carbonate / trans-1,2-Diaminocyclohexane; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness; Sealed vessel View Scheme

Yield

Multi-step reaction with 3 steps
1: sodium t-butanolate / bis(1,5-cyclooctadiene)nickel (0); 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere
2: trifluoroacetic acid; N-iodo-succinimide / 14 h / 23 °C / Inert atmosphere; Sealed vessel
3: potassium carbonate / trans-1,2-Diaminocyclohexane; copper(l) chloride / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere; Darkness; Sealed vessel
View Scheme

: 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%

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

: 507-09-5
thioacetic acid

: 165800-03-3
linezolid

Conditions

Conditions	Yield
Stage #1: (R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one; tiolacetic acid at 23℃; for 7h; Stage #2: With potassium hydroxide In water at 23℃;	90%
at 23℃; for 7h; Inert atmosphere;	90%
Ambient temperature;	86%
at 20℃; for 15h;	85%
at 20℃; for 15h;

: C33H52N2O10

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

: C48H70FN7O13

Conditions

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4h;	86%

: 108-24-7
acetic anhydride

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

: 165800-03-3
linezolid

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃; under 1034.32 Torr; for 3h;	85%
With hydrogen; palladium 10% on activated carbon In dichloromethane under 1103.36 Torr; for 6h;	80%
Stage #1: acetic anhydride; (R)-5-azidomethyl-3-(3-fluoro-4-(morpholin-4-yl)phenyl)oxazolidin-2-one With hydrogen; acetic acid; palladium 10% on activated carbon In ethyl acetate at 25 - 35℃; under 1551.49 Torr; for 3h; Stage #2: With sodium carbonate In water; ethyl acetate for 0.166667h; Product distribution / selectivity;	78%

: 677-25-8
ethylenesulfonyl fluoride

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

: PH-027

Conditions

Conditions	Yield
In ethyl acetate at 100℃; for 16h; Sealed tube;	85%

: 677726-20-4
C40H69NO13

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

: C54H85FN6O16

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; copper(l) iodide In tetrahydrofuran at 20℃; for 2h;	80%

: 1308299-12-8
N-(3,6,9,12-tetraoxapentadec-14-ynyl)-2,3,3a,4,7,7a-hexahydro-1,3-dioxo-4,7-methano-isoindol

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

: 1309042-01-0
(R)-1-(1-(1-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)-1H-1,2,3-triazol-4-yl)-2,5,8,11-tetraoxatridecan-13-yl)-2,3,3a,4,7,7a-hexahydro-1,3-dioxo-4,7-methanoisoindole

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine In acetonitrile at 20℃; for 2h; Inert atmosphere;	75%

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

: 74-86-2
acetylene

: PH-027

Conditions

Conditions	Yield
In 1,2-dimethoxyethane at 90℃; for 12h;	74%

: 762-42-5
dimethyl acetylenedicarboxylate

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

: 503026-28-6
1-[3-(3-fluoro-4-morpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
In 1,2-dimethoxyethane at 90℃; for 24h;	73%

: 23418-85-1
3-butyn-1-yl p-toluenesulfonate

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

: 677726-23-7
C25H28FN5O6S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; copper(l) iodide In tetrahydrofuran at 20℃; for 2h;	63%

: 1423-60-5
methyl ethynyl ketone

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

A: (R)-5-(5-Acetyl-[1,2,3]triazol-1-ylmethyl)-3-(3-fluoro-4-morpholin-4-yl-phenyl)-oxazolidin-2-one

B: 503026-25-3
(R)-5-(4-Acetyl-[1,2,3]triazol-1-ylmethyl)-3-(3-fluoro-4-morpholin-4-yl-phenyl)-oxazolidin-2-one

Conditions

Conditions	Yield
In 1,2-dimethoxyethane at 90℃; for 24h;	A 5% B 62%

...Expand

: 677726-42-0
C33H57NO10

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

: C47H73FN6O13

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; copper(l) iodide In tetrahydrofuran at 20℃; for 15h;	56%

: 87450-10-0
3,6,9,12-tetraoxapentadec-14-yn-1-ol

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

: 1308299-13-9
(R)-3-(3-fluoro-4-morpholinophenyl)-5-((4-(13-hydroxy-2,5,8,11-tetraoxatridecyl)-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine In acetonitrile at 20℃; for 2h; Inert atmosphere;	54%

: 13105-72-1
2-(N-methyl-N-prop-2-yn-1-ylamino)ethanol

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

: C20H27FN6O4

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; copper(l) iodide In tetrahydrofuran at 20℃; for 16h;	50.6%

: 677727-50-3
C43H78N2O12

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

: C57H94FN7O15

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; copper(l) iodide In tetrahydrofuran at 20℃; for 4h;	50%

: C42H74N2O12

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

: C56H90FN7O15

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; copper(l) iodide In tetrahydrofuran at 20℃; for 4h;	50%

: 677727-53-6
C42H76N2O13

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

: C56H92FN7O16

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; copper(l) iodide In tetrahydrofuran at 20℃; for 4h;	50%

: 5390-04-5
pent-1-yn-5-ol

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

: C19H24FN5O4

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; copper(l) iodide In tetrahydrofuran at 20℃; for 16h;	48.7%

: 159428-42-9
1,11-bis(2-propyn-1-oxy)-3,6,9-trioxaundecane

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

: 1308299-19-5
C42H54F2N10O11

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine In acetonitrile at 20℃; for 2h; Inert atmosphere;	47%

: 1308299-10-6
4-amino-1-(3,6,9,12-tetraoxapentadec-14-ynyl)pyrimidin-2(1H)-one

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

: 1308299-15-1
(R)-5-((4-(13-(4-amino-2-oxopyrimidin-1(2H)-yl)-2,5,8,11-tetraoxatridecyl)-1H-1,2,3-triazol-1-yl)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine In acetonitrile at 20℃; for 2h; Inert atmosphere;	46%

(R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone Chemical Properties

Molecular structure of (R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone (CAS NO.168828-84-0) is:

Product Name: (R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone
CAS Registry Number: 168828-84-0
Systematic Name: diazo-[(5R)-3-(3-fluoro-2-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]-methyl-ammonium
Molecular Formula: C₁₄H₁₆FN₅O₃
Molecular Weight: 321.31
SMILES: C[N+](=[N+]=[N-])[C@H]1CN(C(=O)O1)c2cccc(c2N3CCOCC3)F
InChI: InChI=1/C14H17FN5O3/c1-18(17-16)12-9-20(14(21)23-12)11-4-2-3-10(15)13(11)19-5-7-22-8-6-19/h2-4,12H,5-9H2,1H3/q+1/t12-/m1/s1
InChIKey: BZQOTFBTVJNDAL-GFCCVEGCBX
Std. InChI: InChI=1S/C14H17FN5O3/c1-18(17-16)12-9-20(14(21)23-12)11-4-2-3-10(15)13(11)19-5-7-22-8-6-19/h2-4,12H,5-9H2,1H3/q+1/t12-/m1/s1
Std. InChIKey: BZQOTFBTVJNDAL-GFCCVEGCSA-N

(R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone Specification

(R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone , its cas register number is 168828-84-0. It also can be called 2-Oxazolidinone,5-(azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-,(5R)- .

Product Name

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

Synthetic route

(R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone Chemical Properties

(R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone Specification

Related Products

Hot Products