Potassium bisulfate → HCID 22277016, compound

HRID 1063889Notes

Reaction equation

HRID 1063889 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]2S[CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.O[O:22][S:23]([O-:25])=O.[K+].OS([O-])(=O)=O.[K+]>CO>[Br:1][C:2]1[S:6][C:5]([CH:7]2[S:23](=[O:25])(=[O:22])[CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 22276386HCID 22276386, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22277016HCID 22277016, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-(5-bromo-2-thienyl)-4-tert-butoxycarbonylperhydro-1,4-thiazepine (73.8 g) in methanol (500 ml) was added an aqueous solution (500 ml) of OXONE (2KHSO5.KHSO4.K2SO4) (156 g) under ice-cooling. After being stirred for 4 hours, the reaction mixture was concentrated in vacuo to remove methanol. The residue was extracted with ethyl acetate (1000 ml) and the extract was washed successively with a saturated aqueous solution of sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was washed with hexane to afford 7-(5-bromo-2-thienyl)-4-tert-butoxycarbonylperhydro-1,4-thiazepine 1,1-dioxide (64.6 g) as a solid.

Workup

  1. temperatureK2SO4) (156 g) under ice-cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customto remove methanol
  4. extractionThe residue was extracted with ethyl acetate (1000 ml)
  5. washthe extract was washed successively with a saturated aqueous solution of sodium bicarbonate and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-3751c01c48054c0eab91df04266cd8f7
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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