Hydrogen Peroxide → HCID 86689979, compound

HRID 1754047Notes

Reaction equation

HRID 1754047 reaction equation
[C:1]([O:4][CH:5]([CH2:19][CH2:20][S:21][CH3:22])[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:7])(=[O:3])[CH3:2].[OH:23]O>CO>[C:1]([O:4][CH:5]([CH2:19][CH2:20][S:21]([CH3:22])=[O:23])[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 86689978HCID 86689978, compound

Product 1

HCID 86689979HCID 86689979, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(decylamino)-4-(methylthio)-1-oxobutan-2-yl acetate (21.1 g, 63.4 mmol) in methanol (110 mL) at 0° C. was added hydrogen peroxide (30%, 19.43 mL, 190 mmol) and the ice bath was removed. The reaction was allowed to stir for 5.5 hr. The reaction was diluted with water (400 mL) and then extracted with EtOAc (200 mL) to give an emulsion which did not separate after 18 hrs. The emulsion was treated with brine (250 mL) and the layers separated. The aqueous layer was extracted with EtOAc (200 mL) and the combined organic layers were washed with 10% sodium bisulfite. The organic layer was dried over magnesium sulfate, filtered and evaporated to give an orange oil (22.4 g, 100%). m/z 348 (MH+).

Workup

  1. customthe ice bath was removed
  2. additionThe reaction was diluted with water (400 mL)
  3. extractionextracted with EtOAc (200 mL)
  4. customto give an emulsion which
  5. customdid not separate after 18 hrs
  6. additionThe emulsion was treated with brine (250 mL)
  7. customthe layers separated
  8. extractionThe aqueous layer was extracted with EtOAc (200 mL)
  9. washthe combined organic layers were washed with 10% sodium bisulfite
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-4c230e8fc34e412ba17acd5f319ef036
Source dataset
uspto-grants-2015_10
Patent number
US09169203B2

Reaction notes

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