Sodium Thiosulfate → HCID 131732413, compound
Reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:8]=[CH:7][C:6]([C@H:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])(C)C)[CH3:10])=[CH:5][CH:4]=1.[C:21](C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)[CH3:22].ClC1C=CC=C(C(OO)=[O:45])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:14]([O:13][C:12](=[O:18])[NH:11][C@@H:9]([C:6]1[CH:7]=[N+:8]([O-:45])[C:3]([C:2]([F:1])([F:19])[F:20])=[CH:4][CH:5]=1)[CH3:10])[CH2:17][CH2:21][CH3:22]Participants
Conditions
- Temperature
- 50 °C
Procedure
To a solution of tert-butyl {(1R)-1-[6-(trifluoromethyl)-3-pyridinyl]ethyl}carbamate (0.626 g, 2.157 mmol) in chloroform (10.0 mL) were added 2,6-di-tert-butyl-4-methylphenol (24 mg, 0.108 mmol) and 3-chloroperbenzoic acid (0.665 g, 2.70 mmol). The reaction mixture was stirred at 50° C. for 48 h. The reaction mixture was cooled to ambient temperature. Saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate were added. The mixture was extracted with dichloromethane (3×). The combined organics extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (75% hexanes/ethyl acetate→100% ethyl acetate) gave the title compound (140 mg). MS 307.0 (M+1).
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- extractionThe mixture was extracted with dichloromethane (3×)
- washThe combined organics extracts were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customPurification by silica gel chromatography (75% hexanes/ethyl acetate→100% ethyl acetate)
Sources & evidence
- ORD record
- ord-51a6626d665840aea99abfeabc9a025b
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946231B2
Reaction notes
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