Sodium Azide → (5R)-5-azidomethyl-3-(3-fluoro-4-{4-methyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one
Reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[CH:7]=[C:8]([N:20]2[CH2:24][C@H:23]([CH2:25]OS(C)(=O)=O)[O:22][C:21]2=[O:31])[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[CH2:13]1>CN(C=O)C.C(OCC)(=O)C>[N:1]([CH2:25][C@@H:23]1[O:22][C:21](=[O:31])[N:20]([C:8]2[CH:9]=[CH:10][C:11]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[CH2:13]3)=[C:6]([F:5])[CH:7]=2)[CH2:24]1)=[N+:2]=[N-:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
Sodium azide (924 mg) was added to a solution of (5R)-3-(3-fluoro-4-{4-methyl-3-oxopiperazin-1-yl}phenyl)-5-(methanesulfonyloxymethyl)oxazolidin-2-one (950 mg) in dry DMF (50 ml), and the mixture heated at 75° C. for 2 hours. The mixture was diluted with ethyl acetate and washed with three portions of water. The aqueous layer was then back-extracted with two portions of ethyl acetate, and the combined organic extracts dried over MgSO4. Evaporation gave (5R)-5-azidomethyl-3-(3-fluoro-4-{4-methyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one product which was used without further purification.
Workup
- washwashed with three portions of water
- extractionThe aqueous layer was then back-extracted with two portions of ethyl acetate
- dry with materialthe combined organic extracts dried over MgSO4
- customEvaporation
Sources & evidence
- ORD record
- ord-403eb9b6f5d74f4cb10f3c5219b29b47
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06069145
Reaction notes
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