Sodium Azide → 3-[3-Fluoro-4-(4-tert-butoxycarbonylpiperazin-1-yl)phenyl]-5-azidomethyl-2-oxazolidinone

HRID 1078518Notes

Reaction equation

HRID 1078518 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][CH:24]([CH2:26]OS(C)(=O)=O)[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[N-:33]=[N+:34]=[N-:35].[Na+]>CC(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([N:21]2[CH2:25][CH:24]([CH2:26][N:33]=[N+:34]=[N-:35])[O:23][C:22]2=[O:32])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 33557Sodium Azide3×HCID 214626263-[3-Fluoro-4-(4-tert-butoxycarbonylpiperazin-1-yl)phenyl]-5-methanesulfonyloxymethyl-2-oxazolidinone

Product 1

HCID 214626343-[3-Fluoro-4-(4-tert-butoxycarbonylpiperazin-1-yl)phenyl]-5-azidomethyl-2-oxazolidinoneYield 92%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent4×

Procedure

A solution of 440 mg (0.93 mmol) of mesylate 10 in 22 mL acetone was treated with a solution of 604 mg (9.29 mmol) of sodium azide in 6.4 mL water. The mixture was warmed at reflux for 18 hours. The mixture was cooled and a solution of 600 mg of sodium azide in 6 mL water was added followed by warming at reflux for an additional 18 hours. The mixture was cooled and a solution of 1.2 g of sodium azide in 12 mL water was added followed by warming at reflux for 24 hours. The mixture was cooled and diluted with 60 mL water and extracted with ethyl acetate (3×75). The combined organic layers were extracted with 100 mL saturated NaCl solution followed by drying (Na2SO4). Concentration in vacuo afforded 358 mg (92%) of azide 11 as a white solid, mp=130.5° C.-132.5° C., sufficiently pure for use in the next step.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. temperatureby warming
  5. temperatureat reflux for an additional 18 hours
  6. temperatureThe mixture was cooled
  7. temperatureby warming
  8. temperatureat reflux for 24 hours
  9. temperatureThe mixture was cooled
  10. extractionextracted with ethyl acetate (3×75)
  11. extractionThe combined organic layers were extracted with 100 mL saturated NaCl solution
  12. dry with materialby drying (Na2SO4)
  13. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c3e767b3558d484eb2bd9690e3f59595
Source dataset
uspto-grants-1996_08
Patent number
US05547950

Reaction notes

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