Methyl iodide → HCID 19065009, compound

Participants

Reaction Steps

To a solution of 176 mg (0.405 mmol) of N- [2- [4-(tert-butoxycarbonylamino)butyloxy]-4-methylphenyl]benzenesulfonamide in 1.5 mL of anhydrous DMF was added 78.4 mg (0.567 mmol) of powdered anhydrous potassium carbonate and 28 mL (0.446 mmol) of iodomethane. After stirring for 18 h, the mixture was partitioned between 20 mL of ethyl acetate and 20 mL of water. The organic layer was washed with water (2×15 mL), brine (15 mL), dried (Na2SO4) and concentrated to give 180 mg (99%) of the title compound as a colorless syrup. 1 H-NMR (300 MHz, CDCl3) δ 7.70 (m, 2H), 7.56 (m, 1H), 7.46 (m, 2H), 7.14 (d, 1H, J=2.2 Hz), 7.05 (dd, 1H, J=8.4, 2.2 Hz), 6.68 (d, 1H, J=8.4), 4.53 (br s, 1H), 3.61 (t, 2H, J=6.0 Hz), 3.19 (s, 3H), 3.06 (q, 2H, J=6.3 Hz), 2.28 (s, 3H), 1.46 (s, 9H), 1.30-1.41 (m, 4H). Mass spectrum (MALDI-TOF, gentisic acid matrix) calcd. for C23H32 N2O5S: 349.2 (M-BOC+2H). Found: 349.8.

Provenance & Evidence