Sodium Azide → (S)-N-[[3-[4-Azido-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1415900Notes

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

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) δ 8.22, 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-3a8e56af3dc040a2a73f83e1ad42cae3
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05910504

Reaction notes

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