Hydrogen Peroxide → HCID 9845530, compound
Reaction equation
[CH2:1]([C:5]1[CH:10]=[C:9](/[C:11](/[S:25][CH3:26])=[CH:12]/[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[N:8]2[N:27]=[CH:28][CH:29]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].[OH:30]O>C(O)(=O)C.ClCCl>[CH2:1]([C:5]1[CH:10]=[C:9](/[C:11](/[S:25]([CH3:26])=[O:30])=[CH:12]/[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[N:8]2[N:27]=[CH:28][CH:29]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
0.50 g of the compound obtained in Example 12 was dissolved in 5 ml of acetic acid. To the solution was added 0.14 ml of 30% aqueous hydrogen peroxide solution, followed by stirring at room temperature for 4 hours. The reaction mixture was diluted with dichloromethane, washed sequentially with water, sodium bicarbonate solution and saturated saline and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1→ethyl acetate→dichloroethane:methanol=10:1) and recrystallized from ethyl acetate-n-hexane. 0.38 g of the desired compound was obtained as crystals. The structure and melting point of the compound obtained are shown in Table 1.
Workup
- washwashed sequentially with water, sodium bicarbonate solution and saturated saline
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1→ethyl acetate→dichloroethane:methanol=10:1)
- customrecrystallized from ethyl acetate-n-hexane
Sources & evidence
- ORD record
- ord-51b5b10fa509451eafbbf572ffaddb66
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06372749B1
Reaction notes
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