Sodium Thiosulfate → HCID 86666286, compound
Reaction equation
[F:1][C:2]1[C:3]([O:9][CH2:10][C@@H:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])=[N:4][O:5][C:6]=1[CH2:7][OH:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[F:1][C:2]1[C:3]([O:9][CH2:10][C@@H:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])=[N:4][O:5][C:6]=1[CH:7]=[O:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of tert-butyl [(1S)-2-{[4-fluoro-5-(hydroxymethyl)isoxazol-3-yl]oxy}-1-methylethyl]carbamate (164 mg), Dess-Martin periodinane (288 mg) and acetonitrile (3 mL) was stirred at 0° C. for 1 hr, and then at room temperature for 30 min. To the reaction mixture was further added Dess-Martin periodinane (288 mg), and the mixture was stirred at room temperature for 30 min. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a colorless oil (155 mg).
Workup
- waitat room temperature for 30 min
- stirringthe mixture was stirred at room temperature for 30 min
- extractionthe mixture was extracted with ethyl acetate
- washThe obtained organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-15f61055a49c46fd856d64558682587f
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729102B2
Reaction notes
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