Water → (5R)-3-[3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one

HRID 1452586Notes

Reaction equation

HRID 1452586 reaction equation
[N-:1]=[N+]=[N-].[Na+].[N:5]([CH2:8][C@H:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[C:19]([F:21])[C:18](C3CCS(=O)(=O)CC=3)=[C:17](F)[CH:16]=2)[CH2:10]1)=[N+:6]=[N-:7].C(O[CH2:35][CH3:36])(=O)C.O.[CH3:38][N:39]([CH:41]=O)C>C1OCCOCCOCCOCCOCCOC1>[F:21][C:19]1[CH:20]=[C:15]([N:11]2[CH2:10][C@H:9]([CH2:8][N:5]=[N+:6]=[N-:7])[O:13][C:12]2=[O:14])[CH:16]=[CH:17][C:18]=1[N:39]1[CH:38]=[C:35]([CH3:36])[N:1]=[CH:41]1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 86598351HCID 86598351, compound

Product 1

HCID 58840977(5R)-3-[3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-(azidomethyl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Conditions

Temperature
90 °C

Procedure

Sodium azide (0.596 g, 9.08 mmol) and 18-crown-6 (0.025 g, 0.095 mmol) were added to a solution of {(5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl methanesulfonate (WO 01/81350 A1) (3.161 g, 8.56 mmol) in DMF (8.5 ml). The reaction mixture was heated to 90° C. under an atmosphere of nitrogen for 19 hours. It was poured into a mixture of ethyl acetate and water and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and the solvent was removed under vacuum to afford the title compound (1.94 g) as a solid.

Workup

  1. extractionwas extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-0a6ffb47be9248969136eb8b74a3dae2
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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