Triethyl(methoxycarbonylsulfamoyl)aminium → N-[(4aR,6R,8aS)-8a-(5-bromo-2-fluorophenyl)-6-(4-methyl-1,3-oxazol-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Participants

Reaction Steps

Methyl N-(triethylammoniumsulfonyl)carbamate (Burgess reagent) (0.811 g, 3.40 mmol) was added to a solution of (4aR,6R,8aS)-2-(benzoylamino)-8a-(5-bromo-2-fluorophenyl)-N-(1-oxopropan-2-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazine-6-carboxamide (C39) (0.747 g, 1.36 mmol) in toluene (34 mL). The resulting solution was stirred at room temperature for 10 minutes, followed by heating to 65° C. for 16 hours. The reaction mixture was concentrated under reduced pressure. Purification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) afforded the product as a yellow oily residue. Yield: 417 mg, 58%. LCMS m/z 532.1 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 8.17 (br s, 2H), 7.36-7.54 (m, 5H), 7.36 (q, J=1.2 Hz, 1H), 7.01-7.06 (m, 1H), 4.83 (dd, J=12.0, 2.4 Hz, 1H), 4.31 (dd, J=11.9, 1.6 Hz, 1H), 3.07 (dd, J=13.0, 3.8 Hz, 1H), 2.70 (m, 1H), 2.58-2.54 (m, 1H), 2.17 (d, J=1.7 Hz, 3H), 2.08-2.14 (m, 1H).

Provenance & Evidence