Triphenylphosphine → 1-[(1R)-3-chloro-1-(3-chloro-5-fluorophenyl)propyl]-3-isopropyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

Participants

Reaction Steps

To mixture of 1-isopropyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1.28 g, 6.00 mmol), (1S)-3-chloro-1-(3-chloro-5-fluorophenyl)propan-1-ol (1.34 g, 6.00 mmol) and triphenylphosphine (1.73 g, 6.60 mmol, 1.1 equiv.) in tetrahydrofuran (20 mL) under nitrogen was added slowly diisopropyl azodicarboxylate (1.28 mL, 6.60 mmol, 1.1 equiv.) via a syringe at 0° C. The resulting solution was stirred at room temperature overnight. Solvent was removed under reduced pressure and the viscous brown liquid residue was purified using Isco CombiFlash Companion column chromatography (silica gel, 0-15% ethyl acetate/hexane) to give 2.06 g (82%) of 1-[(1R)-3-chloro-1-(3-chloro-5-fluorophenyl)propyl]-3-isopropyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide as a white solid.

Provenance & Evidence