hydroxylamine-O-sulfonic acid → HCID 9906472, compound

HRID 2292987Notes

Reaction equation

HRID 2292987 reaction equation
[F-].C([N+:6](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[CH2:31][CH2:30][CH2:29][C:28]=2[C:32]2[CH:37]=[CH:36][C:35]([S:38](C)(=[O:40])=[O:39])=[CH:34][CH:33]=2)[CH:23]=[CH:24][C:25]=1[F:26].CC([O-])=O.[Na+].NOS(O)(=O)=O>C(OCC)(=O)C.O.C1COCC1>[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[CH2:31][CH2:30][CH2:29][C:28]=2[C:32]2[CH:37]=[CH:36][C:35]([S:38]([NH2:6])(=[O:40])=[O:39])=[CH:34][CH:33]=2)[CH:23]=[CH:24][C:25]=1[F:26]

Participants

8

Reactant 4

HCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 2724141Tetrabutylammonium FluorideHCID 10784091HCID 10784091, compound

Product 1

HCID 9906472HCID 9906472, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride (0.83 mL, 0.83 mmol, 1M in THF) was added to the silane from Step 1 (0.121 g, 0.277 mmol) and dry THF (0.5 mL). The resulting mixture was refluxed for 1 hour then cooled to room temperature. To the reaction mixture was added sequentially NaOAc (0.103 g, 1.26 mmol), water (1.5 mL), and H2NOSO3H (0.157 g, 1.38 mmol) and the reaction was stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (5.0 mL) and water (5.0 mL). The layers were separated, and the organic layer was washed with saturated NaHCO3 (5.0 mL), water (5.0 mL), and brine (5.0 mL) then dried over MgSO4. The solution was filtered, the solids washed with ethyl acetate, and the solvents removed under reduced pressure. The crude product was purified by silica gel chromatography to afford 0.087 g (97%) of product as a white solid.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 hour
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated NaHCO3 (5.0 mL), water (5.0 mL), and brine (5.0 mL)
  4. dry with materialthen dried over MgSO4
  5. filtrationThe solution was filtered
  6. washthe solids washed with ethyl acetate
  7. customthe solvents removed under reduced pressure
  8. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f7b72b9fd0824f11822cca395c36926a
Source dataset
uspto-grants-1997_11
Patent number
US05684195

Reaction notes

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