Sodium Azide → (S)-N-[[3-[4-Azido-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[NH2:8].N([O-])=O.[Na+].[N-:24]=[N+:25]=[N-].[Na+].C([O-])(=O)C.[Na+]>Cl.O>[N:8]([C:7]1[CH:6]=[CH:5][C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[O:11][C:10]2=[O:19])=[CH:3][C:2]=1[F:1])=[N+:24]=[N-:25]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4.0 g(14.96 mmol) of (S)-N-[3-[3-Fluoro-4-aminophenyl]-2-oxo-5-oxazolidinyl]methylacetamide from Example 9 in 40 mL of 6N HCl solution at 0° C. was treated portionwise with 4.12 g(59.84 mmol) of sodium nitrite, followed by stirring at 0° C. for 2 h. The mixture was then treated in several portions with a solution of 1.94 g(29.92 mmol) of sodium azide and 24.52 g(0.30 mol) of sodium acetate in in 50 mL of water. After addition was complete, solution was extracted with ethyl acetate, and the organic layer was dried (Na2SO4) and concentrated in vacuo to afford 4.1 g(93%) of the title compound as a light yellow solid, sufficiently pure for further use. 1H NMR (CDCl3) δ8.22, 7.59, 7.33, 4.72, 4.10, 3.72, 3.40, 1.90.
Workup
- additionAfter addition
- extractionsolution was extracted with ethyl acetate
- dry with materialthe organic layer was dried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3bd32f29fa204163bfe6b2514156419d
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124334
Reaction notes
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