Sodium Hydroxide → Tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate

HRID 81503Notes

Reaction equation

HRID 81503 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

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86688232tert-Butyl [2,6-dimethyl-4-(5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-phenoxy]acetate

Product 1

HCID 86679896Tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. customthe layers were then separated
  2. extractionthe organic layer was subsequently extracted twice with dichloromethane
  3. washThe combined organic phases were washed with 10% strength aqueous sodium bisulfite solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-689997b834d943a48b8a654f0932247a
Source dataset
uspto-grants-2014_09
Patent number
US08846691B2

Reaction notes

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