HCID 19690780, compound → HCID 19690772, compound

HRID 1437Notes

Reaction equation

HRID 1437 reaction equation
C([NH:5][S:6]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[CH:14]([O:17][C:18](=[O:20])[CH3:19])[CH2:15][F:16])(=[O:8])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[C:18]([O:17][CH:14]([C:13]1[CH:12]=[CH:11][S:10][C:9]=1[S:6]([NH2:5])(=[O:7])=[O:8])[CH2:15][F:16])(=[O:20])[CH3:19]

Participants

3

Reactant 1

HCID 19690780HCID 19690780, compound

Product 1

HCID 19690772HCID 19690772, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.4 g (0.0043 mole) of N-t-butyl-3-(1-aceoxy-2-fluoroethyl) -2-thiophenesulfonamide synthesized in Example 2 dissolved in 5 ml of trifluoroacetic acid. The reaction solution was stirred at normal temperature for 12 hours and then concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated. The residue was recrystallized to obtain 750 mg (Yield: 74%) of the pure title compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with aqueous sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customThe residue was recrystallized

Sources & evidence

ORD record
ord-79a672ca3eff441b932b12489c10964b
Source dataset
uspto-grants-1998_03
Patent number
US05726127

Reaction notes

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