Hydrogen Peroxide → HCID 50899674, compound
Reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@@H:7]([C@@H:9]1[C@:26]2(C)[C@H:12]([C:13]3[C@H:23](C[CH2:25]2)[C@:21]2(C)[CH:16]([CH2:17][C:18](=[O:28])[CH2:19][CH2:20]2)C(=O)C=3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].OO.[OH-:32].[Na+].[Cl-].[NH4+].S([O-])([O-])(=[O:38])=S.[Na+].[Na+].[CH2:43]1[CH2:47][O:46][CH2:45][CH2:44]1>>[O:32]1[C@H:17]2[C:18](=[O:28])[CH2:19][C@H:43]3[C@:21]([CH3:20])([C@@H:16]12)[C:23]1[CH2:13][CH2:12][C@@:26]2([CH3:25])[C@@H:44]([CH2:11][CH2:10][C@@H:9]2[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])[C:45]=1[O:46][C:47]3=[O:38]Participants
7
Procedure
Compound 4 (11.0 mg, 0.0276 mmol) obtained in Example 4 was dissolved in THF (1.0 mL), and 30% aqueous hydrogen peroxide (8.5 μL, 0.0828 mmol) and 10% aqueous sodium hydroxide solution (20.1 μL, 0.0551 mmol) were added thereto at 0° C., followed by stirring at room temperature for 40 minutes. A saturated aqueous ammonium chloride solution and a saturated aqueous sodium thiosulfate solution were added to the reaction mixture, followed by extraction with ethyl acetate twice. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield a residue. The residue was purified by preparative thin layer chromatography to obtain the title compound (4.0 mg, 35%).
Workup
- customat 0° C.
- extractionfollowed by extraction with ethyl acetate twice
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto yield a residue
- customThe residue was purified by preparative thin layer chromatography
Sources & evidence
- ORD record
- ord-eb1cc5709d664b6a8bcd10397f37885d
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952003B2
Reaction notes
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