Sodium Azide → (5R)-5-(Azidomethyl)-3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxazolidinone
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH:17]([CH2:19]OS(C3C=CC(C)=CC=3)(=O)=O)[O:16][C:15]2=[O:31])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1.[N-:32]=[N+:33]=[N-:34].[Na+].CC#N.C(Cl)(Cl)Cl>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][N:32]=[N+:33]=[N-:34])[O:16][C:15]2=[O:31])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
The [[3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-p-toluenesulfonate (2.0 g, 4.287 mmol) was dissolved in dry DMF (15 mL) and then treated with solid NaN3 (1.67 g, 25.722 mmol). The reaction was heated to 65° C. (external temperature) for 6 hours, after which the reaction was allowed to cool to ambient temperature, stirring over a long weekend (158 hours). At this point, the reaction was found to be complete by TLC (6% CH3CN/CHCl3, UV short wave). The reaction was diluted with EtOAc (300 mL) and then washed with water (3×250 mL). The aqueous portions were back-extracted with more EtOAc (2×150 mL). The EtOAc portions were combined, dried over Na2SO4, filtered and concentrated under reduced pressure to give 1.447 g (100%) of the title compound as an off-white solid with a melting point of 91.5°-93° C. and a HRMS (M+) calculated for C14H16N5O5FS 337.1009, found 337.1009.
Workup
- temperatureto cool to ambient temperature
- washwashed with water (3×250 mL)
- extractionThe aqueous portions were back-extracted with more EtOAc (2×150 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9834ada7ef5c448e9c3bbbae54d834f3
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05880118
Reaction notes
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