N-t-butyl-3-benzoyloxy-1-pentanesulfonamide → HCID 18467564, compound

HRID 2229458Notes

Reaction equation

HRID 2229458 reaction equation
C([NH:5][S:6]([CH2:9][CH2:10][CH:11]([O:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:12][CH3:13])(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[C:15]([O:14][CH:11]([CH2:12][CH3:13])[CH2:10][CH2:9][S:6]([NH2:5])(=[O:8])=[O:7])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 18467574N-t-butyl-3-benzoyloxy-1-pentanesulfonamide

Product 1

HCID 18467564HCID 18467564, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of N-t-butyl-3-benzoyloxy-1-pentanesulfonamide (90.4 g) and trifluoroacetic acid (200 ml) was stirred overnight at room temperature. Trifluoroacetic acid was removed under reduced pressure and water and chloroform were added to the residue. A saturated aqueous solution of sodium hydrogencarbonate was added thereto with vigorously stirring until the aqueous layer became neutral. After extraction with chloroform, the organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate: hexane/ethyl acetate=2/1 to 1/1) to obtain 3-benzoyloxy-1-pentanesulfonamide (60.6 g) as oil.

Workup

  1. customTrifluoroacetic acid was removed under reduced pressure and water and chloroform
  2. additionwere added to the residue
  3. additionA saturated aqueous solution of sodium hydrogencarbonate was added
  4. stirringwith vigorously stirring until the aqueous layer
  5. extractionAfter extraction with chloroform
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluate: hexane/ethyl acetate=2/1 to 1/1)

Sources & evidence

ORD record
ord-3249c274d15d48eaa429edd69d475f15
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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