Trifluoroacetic acid → HCID 18467544, compound

HRID 2229452Notes

Reaction equation

HRID 2229452 reaction equation
FC(F)(F)C(O)=O.C([NH:12][S:13]([CH2:16][CH:17]([O:21][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:18][CH2:19][CH3:20])(=[O:15])=[O:14])(C)(C)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:22]([O:21][CH:17]([CH2:18][CH2:19][CH3:20])[CH2:16][S:13]([NH2:12])(=[O:15])=[O:14])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 18467634HCID 18467634, compound

Product 1

HCID 18467544HCID 18467544, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic acid (200 ml) was added to N-t-butyl-2-benzoyloxy-1-pentanesulfonamide (132.8 g). After stirring for 32 hours at room temperature, the solution was concentrated under reduced pressure. After further adding trifluoroacetic acid (100 ml) and stirring for 16 hours at room temperature, the solution was concentrated under reduced pressure to obtain an oily substance (165 g). This substance was dissolved in ethyl acetate and, after adding a saturated aqueous solution of sodium hydrogencarbonate, the solution was stirred for 15 minutes at room temperature. The organic layer was washed with 5% brine, dried over sodium sulfate, and concentrated under reduced pressure to obtain 2-benzoyloxy-1-pentanesulfonamide (92.8 g).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionAfter further adding trifluoroacetic acid (100 ml)
  3. stirringstirring for 16 hours at room temperature
  4. concentrationthe solution was concentrated under reduced pressure
  5. customto obtain an oily substance (165 g)
  6. stirringthe solution was stirred for 15 minutes at room temperature
  7. washThe organic layer was washed with 5% brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b26f20bb6e744160b1d41bf9b700da74
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

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