Reaction equation
[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@H:8]([C:24](=[S:26])[NH2:25])[CH2:7]1)(=[O:4])=[O:3].CO[CH:29](OC)[N:30](C)C>>[CH3:1][S:2]([O:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[O:12])[C@H:8]([C:24]2[S:26][N:30]=[CH:29][N:25]=2)[CH2:7]1)(=[O:4])=[O:3]Participants
Procedure
To (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-thiocarbamoylpyrrolidine (1.5 g) was added N,N-dimethylformamide dimethylacetal (1.5 ml) and the mixture was stirred at room temperature for 1.5 hours. After the solvent was removed, the residue was dissolved in dichloromethane (30 ml). To the solution was added dropwise O-(mesitylenesulfonyl)hydroxylamine (1.5 g) in dichloromethane (20 ml) at 0° C. After stirring at room temperature for 2 hours, the mixture was washed with saturated aqueous sodium bicarbonate and brine successively. The dried organic layer was evaporated and the residue was subjected to a column chromatography on silica gel (30 g) eluting with a mixture of n-hexane and ethyl acetate (1:2 V/V) to give (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(1,2,4-thiadiazol-5-yl)pyrrolidine (850 mg).
Workup
- customAfter the solvent was removed
- dissolutionthe residue was dissolved in dichloromethane (30 ml)
- additionTo the solution was added dropwise O-(mesitylenesulfonyl)hydroxylamine (1.5 g) in dichloromethane (20 ml) at 0° C
- stirringAfter stirring at room temperature for 2 hours
- washthe mixture was washed with saturated aqueous sodium bicarbonate and brine successively
- customThe dried organic layer was evaporated
- washeluting with a mixture of n-hexane and ethyl acetate (1:2 V/V)
Sources & evidence
- ORD record
- ord-0dbc7b47e1e448e2b4a219ad357c6f54
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05138064
Linked notes
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