Reaction equation
[CH3:1][C:2]1[CH:16]=[C:15]([C:17]2[O:18][C:19]3[N:20]=[C:21]([S:30][CH3:31])[N:22]=[C:23]([O:26][CH2:27][CH2:28][CH3:29])[C:24]=3[N:25]=2)[CH:14]=[C:13]([CH3:32])[C:3]=1[O:4][CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].ClC1C=CC=C(C(OO)=[O:41])C=1.[OH-:44].[Na+]>ClCCl>[CH3:31][S:30]([C:21]1[N:22]=[C:23]([O:26][CH2:27][CH2:28][CH3:29])[C:24]2[N:25]=[C:17]([C:15]3[CH:16]=[C:2]([CH3:1])[C:3]([O:4][CH2:5][C:6]([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7])=[C:13]([CH3:32])[CH:14]=3)[O:18][C:19]=2[N:20]=1)(=[O:41])=[O:44]Participants
5
Procedure
250 mg of tert-butyl [2,6-dimethyl-4-(5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)phenoxy]acetate were dissolved in 5 ml of dichloromethane. At 0° C., 268 mg of 3-chlorperbenzoic acid were then added, after which the mixture was stirred at room temperature for 12 h. The mixture was treated with 1 M aqueous sodium hydroxide solution, the layers were then separated and the organic layer was subsequently extracted twice with dichloromethane. The combined organic phases were washed with 10% strength aqueous sodium bisulfite solution, dried over sodium sulfate, filtered and evaporated under reduced pressure. This gave 268 mg of the title compound.
Workup
- customthe layers were then separated
- extractionthe organic layer was subsequently extracted twice with dichloromethane
- washThe combined organic phases were washed with 10% strength aqueous sodium bisulfite solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-689997b834d943a48b8a654f0932247a
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846691B2
Linked notes
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