Potassium Carbonate → HCID 59704816, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide (16.55 g, 50 mmol) from Step A, K2CO3 (17.3 g, 125 mmol), and benzyltriethylammonium chloride (1.135 g, 5 mmol) in dried 1,4-dioxane (75 mL) was added methyl(R)-glycidate (15.3 g, 150 mmol). The mixture was sealed and was heated to 70° C. for 24 h. The mixture was then poured into Et2O/H2O (200 mL/200 mL). The organic layer was washed with brine (200 mL), dried (Na2SO4), and filtered. After removal of solvent, the crude product was recrystallized from Et2O/hexane to give 17.8 g of the product (83%) as a pale brown solid. 1H NMR (300 MHz, CDCl3) δ 7.62 (d, J=9.0 Hz, 2H), 7.40 (d, J=9.0 Hz, 2H), 7.10 (d, J=9.0 Hz, 2H), 7.07 (d, J=9.0 Hz, 2H), 4.29 (d, J=6.0 Hz, 1H), 4.03-3.97 (m, 2H), 3.72 (s, 3H), 3.06 (s, 1H, OH), 3.05 (s, 3H); MS (EI) 456 (M++Na, 100), 434 (M++1). Anal. Calcd for C18H18F3NO6S: C, 49.88; H, 4.19; N, 3.23. Found: C, 50.00; H, 4.02; N, 3.22.

Provenance & Evidence