Sodium Azide → (5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one

HRID 459009Notes

Reaction equation

HRID 459009 reaction equation
CS(O[CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[C:15]([F:20])[CH:14]=2)[CH2:8]1)(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[N:21]([CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[C:15]([F:20])[CH:14]=2)[CH2:8]1)=[N+:22]=[N-:23]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 23624705Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester2×

Product 1

HCID 23626594(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-oneYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

[(5R)-3-(3-Fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate (Intermediate 4, 6.14 g, 14.7 mmol) was dissolved in N,N-dimethylformamide (50 ml). Sodium azide (1.92 g, 29.6 mmol) was added and the reaction was stirred at 75° C. overnight. The yellow mixture was poured into half-saturated sodium bicarbonate and extracted using ethyl acetate. The organic layer was washed three times with water, dried (magnesium sulfate), filtered, and concentrated to give the title compound as a yellow solid (4.72 g).

Workup

  1. extractionextracted
  2. washThe organic layer was washed three times with water
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-acfff7b13cf847aa84a0adfd67844734
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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