Sodium Azide → HCID 59191214, compound

HRID 1023957Notes

Reaction equation

HRID 1023957 reaction equation
[CH2:1]([O:8][C:9]1[CH:34]=[C:33]([CH2:35][CH3:36])[CH:32]=[CH:31][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH:21]([CH2:23]OS(C)(=O)=O)[O:20][C:19]2=[O:29])=[CH:14][C:13]=1[F:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:37]=[N+:38]=[N-:39].[Na+]>CN(C=O)C.O>[N:37]([CH2:23][CH:21]1[O:20][C:19](=[O:29])[N:18]([C:15]2[CH:16]=[CH:17][C:12]([O:11][C:10]3[CH:31]=[CH:32][C:33]([CH2:35][CH3:36])=[CH:34][C:9]=3[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:13]([F:30])[CH:14]=2)[CH2:22]1)=[N+:38]=[N-:39]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 59191257HCID 59191257, compound

Product 1

HCID 59191214HCID 59191214, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of methanesulfonic acid 3-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl ester (120 mg, 0.23 mmol) in 2 ml of dry DMF under nitrogen was added sodium azide (57 mg, 0.88 mmol). The reaction mixture was stirred at 75° C. overnight. The reaction mixture was diluted with 15 ml water and extracted with ethyl acetate. The combined organic phase was washed with water, saturated brine solution, dried over anhydrous Na2SO4 and concentrated in vacuo to get 100 mg of the title compound which was used as such for the next step.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phase was washed with water, saturated brine solution
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24365ff6f29f456987a4427ac0ada684
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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