Reaction #2348669

Reaction equation

water

chlorosulfonic acid

(3′S)-3-(3,5-dichlorophenyl)-1′-(3,5-difluorophenyl)-1,3′-bipyrrolidin-2′-one

chlorosulfonic acid

→

4-[(3′S)-3-(3,5-Dichlorophenyl)-2′-oxo-1,3′-bipyrrolidin-1′-yl]-2,6-difluorobenzene-1-sulfonyl chloride

Solvents

DCE

Conditions

Workup

1. 1
   OtherSynthesized
2. 2
   workup.STIRRINGthe reaction mixture stirred at this temperature for 2 hours
3. 3
   workup.STIRRINGthe reaction mixture was stirred at 50° C. for 2 hours
4. 4
   Extractionextracted with EtOAc (3×)
5. 5
   WashThe combined organic extracts were washed with saturated aqueous NaHCO3, water, and brine
6. 6
   Dryingdried (Na2SO4)
7. 7
   Otherevaporated to dryness
8. 8
   OtherThe crude product was used without further purification in the next reaction step

Procedure

Synthesized according to General Procedure 11. To a solution of (3′S)-3-(3,5-dichlorophenyl)-1′-(3,5-difluorophenyl)-1,3′-bipyrrolidin-2′-one (50 mg, 0.12 mmol) in DCE (0.4 mL) at 0° C. was added chlorosulfonic acid (71 mg, 40 μL, 0.61 mmol) dropwise and the reaction mixture stirred from 0° C. to RT over 1 hour, the temperature was raised to 50° C. and the reaction mixture stirred at this temperature for 2 hours. More chlorosulfonic acid was added (71 mg, 40 μL, 0.61 mmol) and the reaction mixture was stirred at 50° C. for 2 hours. The reaction mixture was poured into water and extracted with EtOAc (3×). The combined organic extracts were washed with saturated aqueous NaHCO3, water, and brine, dried (Na2SO4) and evaporated to dryness. The crude product was used without further purification in the next reaction step. (LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=411.3; tR=1.46 min.

Source