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

HRID 1940644
Notes
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Reaction equation

HRID 1940644 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 180AcetoneSolvent
HCID 962
Water
Solvent
4×

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-498d9cb7e79c4282853a240a95710bb0
Source dataset
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05700799

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes