Dichloromethane → HCID 9831417, compound

Participants

Reaction Steps

To a stirred light suspension of 4-[(4-chlorophenyl)sulfonylaminocarbonyl]benzoic acid (0.68 g, 2.02 mmol; EP Pat. Appl. Publ. No. 0189305 B1) in CH2Cl2 (18 mL) and DMF (2 mL) under argon is added oxalyl chloride (0.18 mL, 2.02 mmol) dropwise. After 50 minutes, add a solution of 51 (0.81 g, 2.02 mmol) and NMM (1.00 mL, 9.07 mmol) in CH2Cl2 (8 mL). Stir for 3 hours and then pour the reaction mixture into H2O (75 mL) and separate the layers. The aqueous phase is extracted with additional EtOAc (2×35 mL) and the combined organic extracts are washed with 1N aqueous hydrochloric acid (2×30 mL) followed by brine (30 mL). Drying (MgSO4) and concentration gives crude 54. Purification by flash chromatography [gradient (54-74%) of EtOAc in hexane containing 1% acetic acid] gives 54 [0.96 g (70%), (1:1::LLL:LLD)] as a white solid foam.

Provenance & Evidence