Product Name

  • Name

    Torezolid

  • EINECS 815-370-6
  • CAS No. 856866-72-3
  • Article Data19
  • CAS DataBase
  • Density 1.57
  • Solubility
  • Melting Point 201 °C
  • Formula C17H15FN6O3
  • Boiling Point 614.5±65.0 °C(Predicted)
  • Molecular Weight 370.343
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 856866-72-3 (Torezolid)
  • Hazard Symbols
  • Synonyms Torezolid
  • PSA 106.26000
  • LogP 1.46070

Synthetic route

C23H29FN6O3Si

C23H29FN6O3Si

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With cesium fluoride In tetrahydrofuran at 20℃; for 1h;99%
3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester
1220910-89-3

3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tert.-butyl lithium; (R)-glycidyl butyrate In tetrahydrofuran at 0 - 30℃; for 15h; Reagent/catalyst; Large scale;95%
3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester
1220910-89-3

3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester

(R)-glycidyl butyrate
60456-26-0

(R)-glycidyl butyrate

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Stage #1: 3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester With potassium tert-butylate; lithium tert-butoxide In tetrahydrofuran; acetonitrile at 25℃; for 2h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate In tetrahydrofuran; acetonitrile for 3h;		86.7%
Stage #1: 3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 1.41667h; Inert atmosphere;
Stage #2: (R)-glycidyl butyrate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran at 20℃; for 15h; Inert atmosphere; cooling with ice;		85%
Stage #1: 3-fluoro-4-(6-(2-methyl-2H-tetrazole-5-yl)pyridin-3-yl)phenyl-carbamic acid benzylester With lithium hexamethyldisilazane In tetrahydrofuran at 10 - 15℃; for 2h; Inert atmosphere; Large scale;
Stage #2: (R)-glycidyl butyrate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran at 0 - 15℃; Inert atmosphere; Large scale;		84.4%
2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1056039-83-8

2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

(5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one
444335-16-4

(5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,4-dioxane at 20℃; Reagent/catalyst; Solvent; Temperature; Reflux; Inert atmosphere;84%
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tricyclohexylphosphine In 1,4-dioxane; water for 4h; Reagent/catalyst; Solvent; Suzuki Coupling; Inert atmosphere; Reflux;78%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Solvent; Reflux; Inert atmosphere;63.7%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate Suzuki Coupling;
Stage #1: 2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine; (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 60℃; for 5h; Suzuki Coupling; Inert atmosphere; Large scale;
Stage #2: With L-Cysteine; triethylamine at 60℃; for 16h; Inert atmosphere; Darkness; Large scale;
(5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one
444335-16-4

(5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine
380380-64-3

5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Stage #1: (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; bis(pinacol)diborane In dimethyl sulfoxide at 80℃; for 14h; Inert atmosphere;
Stage #2: 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 70℃; for 3h; Inert atmosphere;		83%
(5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one
487041-08-7

(5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one

2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
1056039-83-8

2-(2-methyl-2H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Suzuki Coupling; Sealed tube; Inert atmosphere; Green chemistry;77.6%
(5R)-3-[3-fluoro-4-(tributylstannyl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one

(5R)-3-[3-fluoro-4-(tributylstannyl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one

5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine
380380-64-3

5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium chloride In N,N-dimethyl-formamide at 90℃; for 4h; Temperature; Reagent/catalyst;48%
With lithium chloride; bis-triphenylphosphine-palladium(II) chloride In 1-methyl-pyrrolidin-2-one at 20 - 120℃; for 4h;26%
With bis-triphenylphosphine-palladium(II) chloride; lithium chloride In 1-methyl-pyrrolidin-2-one at 120℃; for 4h; Stille coupling; Inert atmosphere;26%
With bis-triphenylphosphine-palladium(II) chloride; lithium chloride at 120℃; for 4h;
2,5-dibromopyridine
624-28-2

2,5-dibromopyridine

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium cyanide / N,N-dimethyl-formamide / 7 h / 150 °C / Inert atmosphere
2: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere
3: sodium hydroxide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
4: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere
View Scheme
2-Cyano-5-bromopyridine
97483-77-7

2-Cyano-5-bromopyridine

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere
2: sodium hydroxide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere
View Scheme
meta-fluoroaniline
372-19-0

meta-fluoroaniline

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate / tetrahydrofuran / 2 h / 0 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
2.2: 26 h / -78 - 20 °C / Inert atmosphere
3.1: N-iodo-succinimide; trifluoroacetic acid / 3 h / 20 °C
4.1: potassium carbonate; palladium diacetate / N,N-dimethyl-formamide; water / 6 h / 90 °C / Sealed tube; Inert atmosphere; Green chemistry
View Scheme
Multi-step reaction with 5 steps
1: ethanol / 12 h / Reflux
2: triethylamine / N,N-dimethyl-formamide / 4 h / 65 °C
3: trifluorormethanesulfonic acid; N-iodo-succinimide / dichloromethane / 2 h / 0 °C
4: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h
5: lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 4 h / 90 °C
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydrogencarbonate / dichloromethane / 20 - 25 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -65 - -60 °C / Inert atmosphere
2.2: 20 h / -65 - 25 °C / Inert atmosphere
3.1: trifluoroacetic acid; N-iodo-succinimide / 0.17 h / 20 - 25 °C
3.2: 4 h / 20 - 25 °C
4.1: dmap / toluene / 7 h / 45 - 50 °C
5.1: tris-(o-tolyl)phosphine; potassium carbonate / dimethyl sulfoxide / 20 - 25 °C / Inert atmosphere
5.2: 5.17 h / 20 - 85 °C / Inert atmosphere
6.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 4 h / 95 - 100 °C / Inert atmosphere
7.1: triphenylphosphine; diethylazodicarboxylate / dichloromethane / 5 h / 20 - 25 °C / Inert atmosphere
7.2: 3 h / 20 - 25 °C
View Scheme
N-(carbobenzyloxy)-3-fluoroaniline
149524-47-0

N-(carbobenzyloxy)-3-fluoroaniline

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C / Inert atmosphere
1.2: 26 h / -78 - 20 °C / Inert atmosphere
2.1: N-iodo-succinimide; trifluoroacetic acid / 3 h / 20 °C
3.1: potassium carbonate; palladium diacetate / N,N-dimethyl-formamide; water / 6 h / 90 °C / Sealed tube; Inert atmosphere; Green chemistry
View Scheme
(5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one
149524-42-5

(5R)-3-(3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-iodo-succinimide; trifluoroacetic acid / 3 h / 20 °C
2: potassium carbonate; palladium diacetate / N,N-dimethyl-formamide; water / 6 h / 90 °C / Sealed tube; Inert atmosphere; Green chemistry
View Scheme
Multi-step reaction with 3 steps
1: trifluorormethanesulfonic acid; N-iodo-succinimide / dichloromethane / 2 h / 0 °C
2: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h
3: lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 4 h / 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: trifluoroacetic acid; N-iodo-succinimide / 0.17 h / 20 - 25 °C
1.2: 4 h / 20 - 25 °C
2.1: dmap / toluene / 7 h / 45 - 50 °C
3.1: tris-(o-tolyl)phosphine; potassium carbonate / dimethyl sulfoxide / 20 - 25 °C / Inert atmosphere
3.2: 5.17 h / 20 - 85 °C / Inert atmosphere
4.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 4 h / 95 - 100 °C / Inert atmosphere
5.1: triphenylphosphine; diethylazodicarboxylate / dichloromethane / 5 h / 20 - 25 °C / Inert atmosphere
5.2: 3 h / 20 - 25 °C
View Scheme
5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine
380380-64-3

5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 80 °C / Sealed tube; Inert atmosphere
2: potassium carbonate; palladium diacetate / N,N-dimethyl-formamide; water / 6 h / 90 °C / Sealed tube; Inert atmosphere; Green chemistry
View Scheme
Multi-step reaction with 2 steps
1.1: tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate / tetrahydrofuran / 20 - 70 °C / Inert atmosphere; Large scale
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 10 - 15 °C / Inert atmosphere; Large scale
2.2: 0 - 15 °C / Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 2 steps
1.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium carbonate / 1,4-dioxane; water / 1 h / 70 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 10 - 15 °C / Inert atmosphere; Large scale
2.2: 0 - 15 °C / Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 2 steps
1.1: potassium acetate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 4 h / 70 °C / Inert atmosphere; Large scale
2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,4-dioxane / 5 h / 60 °C / Inert atmosphere; Large scale
2.2: 16 h / 60 °C / Inert atmosphere; Darkness; Large scale
View Scheme
(3-fluoro-phenyl)-carbamic acid methyl ester
72755-13-6

(3-fluoro-phenyl)-carbamic acid methyl ester

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -65 - -60 °C / Inert atmosphere
1.2: 20 h / -65 - 25 °C / Inert atmosphere
2.1: trifluoroacetic acid; N-iodo-succinimide / 0.17 h / 20 - 25 °C
2.2: 4 h / 20 - 25 °C
3.1: dmap / toluene / 7 h / 45 - 50 °C
4.1: tris-(o-tolyl)phosphine; potassium carbonate / dimethyl sulfoxide / 20 - 25 °C / Inert atmosphere
4.2: 5.17 h / 20 - 85 °C / Inert atmosphere
5.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 4 h / 95 - 100 °C / Inert atmosphere
6.1: triphenylphosphine; diethylazodicarboxylate / dichloromethane / 5 h / 20 - 25 °C / Inert atmosphere
6.2: 3 h / 20 - 25 °C
View Scheme
(5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one
487041-08-7

(5R)-3-(3-fluoro-4-iodo-phenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dmap / toluene / 7 h / 45 - 50 °C
2.1: tris-(o-tolyl)phosphine; potassium carbonate / dimethyl sulfoxide / 20 - 25 °C / Inert atmosphere
2.2: 5.17 h / 20 - 85 °C / Inert atmosphere
3.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 4 h / 95 - 100 °C / Inert atmosphere
4.1: triphenylphosphine; diethylazodicarboxylate / dichloromethane / 5 h / 20 - 25 °C / Inert atmosphere
4.2: 3 h / 20 - 25 °C
View Scheme
tert-butyl [(5R)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl carbonate

tert-butyl [(5R)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl carbonate

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tris-(o-tolyl)phosphine; potassium carbonate / dimethyl sulfoxide / 20 - 25 °C / Inert atmosphere
1.2: 5.17 h / 20 - 85 °C / Inert atmosphere
2.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 4 h / 95 - 100 °C / Inert atmosphere
3.1: triphenylphosphine; diethylazodicarboxylate / dichloromethane / 5 h / 20 - 25 °C / Inert atmosphere
3.2: 3 h / 20 - 25 °C
View Scheme
tert-butyl {(5R)-3-[4-(6-cyanopyridin-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl carbonate

tert-butyl {(5R)-3-[4-(6-cyanopyridin-3-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl carbonate

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 4 h / 95 - 100 °C / Inert atmosphere
2.1: triphenylphosphine; diethylazodicarboxylate / dichloromethane / 5 h / 20 - 25 °C / Inert atmosphere
2.2: 3 h / 20 - 25 °C
View Scheme
tert-butyl [(5R)-3-{3-fluoro-4-[6-(2H-tetrazol-5-yl)pyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl carbonate

tert-butyl [(5R)-3-{3-fluoro-4-[6-(2H-tetrazol-5-yl)pyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl carbonate

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Stage #1: tert-butyl [(5R)-3-{3-fluoro-4-[6-(2H-tetrazol-5-yl)pyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl carbonate With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20 - 25℃; for 5h; Inert atmosphere;
Stage #2: With trifluoroacetic acid In dichloromethane at 20 - 25℃; for 3h; Further stages;
(2R)-2-hydroxy-3-[(3-fluorophenyl)amino]propyl butanoate

(2R)-2-hydroxy-3-[(3-fluorophenyl)amino]propyl butanoate

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / N,N-dimethyl-formamide / 4 h / 65 °C
2: trifluorormethanesulfonic acid; N-iodo-succinimide / dichloromethane / 2 h / 0 °C
3: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 4 h
4: lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 4 h / 90 °C
View Scheme
(5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one
444335-16-4

(5R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 60 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 0.5 h
3.1: bis[2-(diphenylphosphino)phenyl] ether; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran; hexane / 12 h / 20 °C
4.1: cesium fluoride / tetrahydrofuran / 1 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 60 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 0.5 h
3.1: bis[2-(diphenylphosphino)phenyl] ether; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran; hexane / 12 h / 20 °C
4.1: cesium fluoride / tetrahydrofuran / 1 h / 20 °C
View Scheme
(R)-3-(4-bromo-3-fluoro-phenyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-oxazolidin-2-one
1188330-70-2

(R)-3-(4-bromo-3-fluoro-phenyl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-oxazolidin-2-one

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 0.5 h
2.1: bis[2-(diphenylphosphino)phenyl] ether; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran; hexane / 12 h / 20 °C
3.1: cesium fluoride / tetrahydrofuran / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 0.5 h
2.1: bis[2-(diphenylphosphino)phenyl] ether; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran; hexane / 12 h / 20 °C
3.1: cesium fluoride / tetrahydrofuran / 1 h / 20 °C
View Scheme
C16H23ClFNO3SiZn

C16H23ClFNO3SiZn

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: bis[2-(diphenylphosphino)phenyl] ether; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran; hexane / 12 h / 20 °C
2: cesium fluoride / tetrahydrofuran / 1 h / 20 °C
View Scheme
2-fluoro-4-(benzyloxycarbonyl)aminophenylboronic acid
874290-59-2

2-fluoro-4-(benzyloxycarbonyl)aminophenylboronic acid

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium carbonate / 1,4-dioxane; water / 1 h / 70 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 10 - 15 °C / Inert atmosphere; Large scale
2.2: 0 - 15 °C / Inert atmosphere; Large scale
View Scheme
(4-bromo-3-fluorophenyl)carbamic acid benzyl ester
510729-01-8

(4-bromo-3-fluorophenyl)carbamic acid benzyl ester

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 10 - 15 °C / Inert atmosphere
2.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 35 - 85 °C / Inert atmosphere
3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 10 - 15 °C / Inert atmosphere; Large scale
3.2: 0 - 15 °C / Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: cobaltocene / tetrahydrofuran / 20 - 30 °C / Inert atmosphere; Large scale
2.1: tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate / tetrahydrofuran / 20 - 70 °C / Inert atmosphere; Large scale
3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 10 - 15 °C / Inert atmosphere; Large scale
3.2: 0 - 15 °C / Inert atmosphere; Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / -75 - -70 °C / Inert atmosphere; Cooling with acetone-dry ice
1.2: Inert atmosphere
2.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium carbonate / 1,4-dioxane; water / 1 h / 70 °C / Inert atmosphere
3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 10 - 15 °C / Inert atmosphere; Large scale
3.2: 0 - 15 °C / Inert atmosphere; Large scale
View Scheme
C14H11BrFNO2Zn

C14H11BrFNO2Zn

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate / tetrahydrofuran / 20 - 70 °C / Inert atmosphere; Large scale
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 10 - 15 °C / Inert atmosphere; Large scale
2.2: 0 - 15 °C / Inert atmosphere; Large scale
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridine-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridine-5-yl)-3-fluorophenyl)-5-hydroxymethyl oxazolidin-2-one dihydrogen phosphate

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In tetrahydrofuran at 0℃; for 3h;97%
Stage #1: (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one With triethylamine; trichlorophosphate In tetrahydrofuran at 0 - 2.2℃; for 3.73333h;
Stage #2: With water In tetrahydrofuran at 11.9℃; for 1h; cooling with ice/salt;		96%
Stage #1: (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one With triethylamine In tetrahydrofuran at 0℃;
Stage #2: With trichlorophosphate In tetrahydrofuran at 1 - 2℃; for 3h;		84.8%
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

4-(2,2-bis(diisopropoxyphosphoryl)ethyl)benzoic acid

4-(2,2-bis(diisopropoxyphosphoryl)ethyl)benzoic acid

(R)-(3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl 4-(2,2-bis(diisopropoxyphosphoryl)ethyl)benzoate

(R)-(3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl 4-(2,2-bis(diisopropoxyphosphoryl)ethyl)benzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;95%
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

benzyl alcohol
100-51-6

benzyl alcohol

dibenzyl (R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl phosphoric acid

dibenzyl (R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl phosphoric acid

Conditions
ConditionsYield
Stage #1: (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one With N-ethyl-N,N-diisopropylamine; trichlorophosphate In tetrahydrofuran at 0 - 20℃; for 4h;
Stage #2: benzyl alcohol With N-ethyl-N,N-diisopropylamine at 0 - 20℃; for 8h;		84%
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

dibenzyl N,N-diisopropylphosphoroamidate
124575-22-0

dibenzyl N,N-diisopropylphosphoroamidate

dibenzyl (R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl phosphoric acid

dibenzyl (R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl phosphoric acid

Conditions
ConditionsYield
Stage #1: (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one; dibenzyl N,N-diisopropylphosphoroamidate With 1H-tetrazole In dichloromethane at 25 - 30℃; for 0.5h;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 5 - 10℃; for 0.5h;		83.1%
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one
856867-59-9

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.5h;82%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;82%
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

dibenzyl (R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl phosphoric acid

dibenzyl (R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl phosphoric acid

Conditions
ConditionsYield
Stage #1: (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one With sodium hydride In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; Cooling with ice;
Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;		82%
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

tetraisopropyl (2-(4-(azidocarbonyl)phenyl)ethane-1,1-diyl)bis(phosphonate)

tetraisopropyl (2-(4-(azidocarbonyl)phenyl)ethane-1,1-diyl)bis(phosphonate)

C38H50FN7O10P2

C38H50FN7O10P2

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 80℃; for 3h;81%
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-fluoromethyloxazolidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-fluoromethyloxazolidin-2-one

Conditions
ConditionsYield
With diethylamino-sulfur trifluoride; triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;75%
With diethylamino-sulfur trifluoride; triethylamine In dichloromethane for 24h;
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

di-tert-butyl diisopropylphosphoramide
137348-86-8

di-tert-butyl diisopropylphosphoramide

(R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl phosphoric acid di-tert-butyl ester

(R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl phosphoric acid di-tert-butyl ester

Conditions
ConditionsYield
Stage #1: (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one; di-tert-butyl diisopropylphosphoramide With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 15h;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran; dichloromethane at -78℃; for 4h;		71%
Stage #1: (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one; di-tert-butyl diisopropylphosphoramide With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20℃; for 15h;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran; dichloromethane at -78℃; for 2h;		68%
Stage #1: (5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one; di-tert-butyl diisopropylphosphoramide With 1H-tetrazole In tetrahydrofuran; dichloromethane at 20 - 25℃; for 16h;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran; dichloromethane at -70 - 25℃; for 2h;
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

isoxazol-3-ol
5777-20-8

isoxazol-3-ol

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(isoxazol-3-yl)oxymethyloxazolidin-2-one
717116-80-8

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(isoxazol-3-yl)oxymethyloxazolidin-2-one

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 12h; Mitsunobu reaction; Inert atmosphere;51%
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

C34H29F2N12O8P
1256966-02-5

C34H29F2N12O8P

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In tetrahydrofuran at 20 - 25℃; for 16h; Inert atmosphere;20%
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

BOC-glycine
4530-20-5

BOC-glycine

C24H26FN7O6

C24H26FN7O6

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide) at 20℃; for 10h;
With dmap; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 10h; Inert atmosphere;
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl disodium phosphate

(R)-[3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl disodium phosphate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethyl phosphate; trichlorophosphate / 2 h / 20 °C / Inert atmosphere
2: sodium methylate / methanol / 2 h / 20 °C / Inert atmosphere
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(methoxymethyl)oxazolidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(methoxymethyl)oxazolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: methanol / 24 h / 20 °C / Inert atmosphere
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(S)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(dimethylaminomethyl)oxazolidin-2-one

(S)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(dimethylaminomethyl)oxazolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / 30 h / 60 °C / Inert atmosphere
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-([1,2,4]triazol-1-yl)methyloxazolidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-([1,2,4]triazol-1-yl)methyloxazolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 48 h / 20 °C / Inert atmosphere
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

A

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-([1,2,3]triazol-1-yl)methyloxazolidin-2-one
700370-32-7

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-([1,2,3]triazol-1-yl)methyloxazolidin-2-one

B

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-([1,2,3]triazol-2-yl)methyloxazolidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-([1,2,3]triazol-2-yl)methyloxazolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 48 h / 20 °C / Inert atmosphere
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(azidomethyl)oxazolidin-2-one
1293990-05-2

(R)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(azidomethyl)oxazolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(S)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(aminomethyl)oxazolidin-2-one
1293990-06-3

(S)-3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-5-(aminomethyl)oxazolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere
3: 10% palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)-2-methoxyacetamide
1293990-07-4

(S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)-2-methoxyacetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere
3: 10% palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
4: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)furan-2-carboxamide
1293990-08-5

(S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)furan-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere
3: 10% palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
4: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)thiopene-2-carboxamide
1293990-09-6

(S)-N-((3-(4-(2-(2-methyltetrazol-5-yl)pyridin-5-yl)-3-fluorophenyl)-2-oxo-oxazolidin-5-yl)methyl)thiopene-2-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere
3: 10% palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
4: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one
856866-72-3

(5R)-3-{3-fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)pyridra-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazoiidin-2-one

(S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
1293990-10-9

(S)-2-(benzyloxy)-N-((3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
2: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere
3: 10% palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
4: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme

3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone Chemical Properties

Molecular structure of 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone (CAS NO.856866-72-3) is:

Product Name: 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone
CAS Registry Number: 856866-72-3
Molecular Formula: C17H15FN6O3
Molecular Weight: 370.34
Density: 1.57 g/cm3
Classification Code: Antibiotic

3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone Specification

 3-[3-Fluoro-4-[6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl]phenyl]-5-(hydroxymethyl)-2-oxazolidinone , its cas register number is 856866-72-3. It also can be called Torezolid [USAN] ; Torezolid ;  (5R)-3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)-5-(hydroxymethyl)oxazolidin-2-one ;  2-Oxazolidinone, 3-(3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)-3-pyridinyl)phenyl)-5-(hydroxymethyl)-, (5R)- .It is an oxazolidinone drug in phase-II clinical trials for complicated skin and skin-structure infections (cSSSI), including those caused by Methicillin-resistant Staphylococcus aureus (MRSA).

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