Reaction #1533

Reaction equation

N-t-butyl-3-(1-aceoxy-2-fluoroethyl) 2-thiophenesulfonamide

N-t-butyl-3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide

→

pure title compound

Yield 74.0%

3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide

Yield 74.0%

Solvents

trifluoroacetic acid

Conditions

Workup

1. 1
   Concentrationconcentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methylene chloride
3. 3
   Washwashed with aqueous sodium bicarbonate solution
4. 4
   OtherThe organic layer was separated
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe filtrate was concentrated
8. 8
   OtherThe residue was recrystallized

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.

Source