Hydrochloric Acid → HCID 69113286, compound

Participants

Reaction Conditions

Reaction Steps

Hydrochloride compound 53 (2.1 g, 5.37 mmol) was dissolved in CH2Cl2 (35 mL) and cooled to 0-5° C. N,N-Diisopropylethylamine (1.87 mL, 11.0 mmol) was added to the above solution followed by addition of p-toluenesulfonyl chloride (0.85 g, 4.46 mmol) in small portions. The reaction mixture was then warmed up to room temperature and stirred overnight. The solvent was removed under reduced pressure and the residual oil was taken up in EtOAc (50 mL). The organic layer was washed with 2.0 M HCl (1×10 mL), saturated NaHCO3 (1×10 mL), and brine (1×25 mL). The resulting EtOAc layer was dried and concentrated under reduced pressure to yield an oil. Flash chromatography (30-50% ethyl acetate in hexane containing 1% acetic acid) yielded the desired sulfonamide 54 (1.1 g, 40%). 1H NMR (DMSO-d6): 8.10 (d, J=9.6 Hz, 1H), 7.55 (d, J=8.0 Hz, 2H), 7.51 (d, J=8.4 Hz, 2H), 7.48 (d, J=8.4 Hz, 2H), 7.30 (d, J=8.4 Hz, 2H), 7.23 (d, J=8.0 Hz, 2H), 7.18 (d, J=8.4 Hz, 2H), 4.33 (m, 1H), 3.59 (s, 3H), 2.81-2.90 (m, 3H), 2.75 (s, 3H), 2.62-2.68 (m, 3H), 2.53 (s, 3H), 2.26(s, 3H).

Provenance & Evidence