Sodium Azide → (5R)-5-Azidomethyl-3-(4-(4-t-butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-oxazolidin-2-one

HRID 2299019Notes

Reaction equation

HRID 2299019 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26]OS(C)(=O)=O)[O:23][C:22]3=[O:32])=[CH:17][C:16]=2[F:33])[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N-:34]=[N+:35]=[N-:36].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O.O>[N:34]([CH2:26][C@@H:24]1[O:23][C:22](=[O:32])[N:21]([C:18]2[CH:19]=[CH:20][C:15]([N:13]3[CH:14]=[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])[N:11]=[CH:12]3)=[C:16]([F:33])[CH:17]=2)[CH2:25]1)=[N+:35]=[N-:36]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 59591362(5R)-3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyloxazolidin-2-one

Product 1

HCID 57114338(5R)-5-Azidomethyl-3-(4-(4-t-butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-oxazolidin-2-oneYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(5R)-3-(4-(4-t-Butyldimethylsilyloxymethylimidazol-1-yl)-3-fluorophenyl)-5-methanesulfonyloxymethyloxazolidin-2-one (13.6 g) was dissolved in dry N,N-dimethylformamide (110 ml). Sodium azide (3.53 g) was added, and the mixture was heated at 80° C. for 3.5 hours. The mixture was cooled, diluted with water (1.1 L) containing sodium bicarbonate (2 g), and extracted with ethyl acetate (2×800 ml). Combined organics were washed with water (2×300 ml), then brine, and dried over magnesium sulfate. The solution was evaporated to a small volume (˜100 ml), and insolubles filtered. The ethyl acetate soluble material was columned on silica (100 g), eluting with ethyl acetate. Product fractions were combined and evaporated to give a gum (10.0 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (2×800 ml)
  3. washCombined organics were washed with water (2×300 ml)
  4. dry with materialbrine, and dried over magnesium sulfate
  5. customThe solution was evaporated to a small volume (˜100 ml), and insolubles
  6. filtrationfiltered
  7. washeluting with ethyl acetate
  8. customevaporated

Sources & evidence

ORD record
ord-dc0121f5a4bf4f99b4f7302ab9237010
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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