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

Temperatur

50 °C

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.

1. customSynthesized
2. stirringthe reaction mixture stirred at this temperature for 2 hours
3. stirringthe reaction mixture was stirred at 50° C. for 2 hours
4. extractionextracted with EtOAc (3×)
5. washThe combined organic extracts were washed with saturated aqueous NaHCO3, water, and brine
6. dry with materialdried (Na2SO4)
7. customevaporated to dryness
8. customThe crude product was used without further purification in the next reaction step

ORD-Eintrag

ord-46cf70a3e2a843f1ab930520dbc00d26

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08143297B2