Sodium Azide → HCID 59996364, compound

HRID 1814039Notes

Reaction equation

HRID 1814039 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[CH:7]=[C:8]([N:18]2[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]2=[O:28])[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH:16]2[CH:14]([O:15]2)[CH2:13]1>CC(C)=O.O>[N:1]([CH:16]1[CH:14]([OH:15])[CH2:13][N:12]([C:11]2[CH:10]=[CH:9][C:8]([N:18]3[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]3=[O:28])=[CH:7][C:6]=2[F:5])[CH2:17]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86759632HCID 86759632, compound

Product 1

HCID 59996364HCID 59996364, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
55 °C

Procedure

Sodium azide (42 mg, 0.64 mmol) was added to a solution of N-({(5S)-3-[3-fluoro-4-(6-oxa-3-azabicyclo[3.1.0]hex-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (36 mg, 0.107 mmol, prepared using the general procedure described for Example 40) in 2:1 acetone-H2O (1.0 mL) and the solution heated at 55° C. for 16 hours. The solution was cooled, concentrated to remove acetone, diluted with water and extracted with chloroform. Combined organic extracts were dried (MgSO4), filtered and concentrated to provide the title compound. This material was used directly in the next reaction. MS (m/z): [M+H]+=379

Workup

  1. customprepared
  2. temperatureThe solution was cooled
  3. concentrationconcentrated
  4. customto remove acetone
  5. additiondiluted with water
  6. extractionextracted with chloroform
  7. dry with materialCombined organic extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-971b72e9394e4a258f24ba5363011308
Source dataset
uspto-grants-2005_04
Patent number
US06875784B2

Reaction notes

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