Sodium Azide → (5R)-5-azidomethyl-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22]OS(C)(=O)=O)[O:19][C:18]2=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[C:10](=[O:16])[CH2:9]1.[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C>[N:29]([CH2:22][C@@H:20]1[O:19][C:18](=[O:28])[N:17]([C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[C:10](=[O:16])[CH2:9]3)=[C:2]([F:1])[CH:3]=2)[CH2:21]1)=[N+:30]=[N-:31]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
(5R)-3-(3-Fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)-oxazolidin-2-one (950 mg) was dissolved in dry DMF (30 ml) and sodium azide (893 mg) was added. The mixture was heated at 80° C. for 5 hours, and then evaporated to dryness. The residue was dissolved in ethyl acetate and the resulting solution washed with water and dried (MgSO4). The crude product so obtained was chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 6% methanol in dichloromethane. Relevant fractions were combined and evaporated to give (5R)-5-azidomethyl-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one (777 mg).
Workup
- customevaporated to dryness
- dissolutionThe residue was dissolved in ethyl acetate
- washthe resulting solution washed with water
- dry with materialdried (MgSO4)
- customThe crude product so obtained
- customwas chromatographed on silica
- temperaturea gradient increasing in polarity from 0 to 6% methanol in dichloromethane
- customevaporated
Sources & evidence
- ORD record
- ord-46b7265681934031ac0c0f6eddd1ef5d
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06069145
Reaction notes
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