Acetic Anhydride → HCID 10278068, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 3H (57.7 g) in formic acid (200 mL) was treated with a mixture of acetic anhydride (35 mL) in formic acid (35 mL) over 10 minutes, stirred for 10 minutes, and concentrated. The concentrate was dissolved in ethyl acetate (500 mL), washed sequentially with 1:1/water:brine, saturated NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was dissolved in warm (60° C.) toluene, cooled, and filtered. The solid was washed with 1:1/toluene:heptane then dried under vacuum (100 mm Hg) at 50° C. with a nitrogen bleed to provide 51.7 g of the desired product. 1H NMR (300 MHz, DMSO-d6) δ8.42 (br s, 0.5H), 8.38 (br s, 0.5H), 8.32 (br s, 0.5H), 8.10 (br s, 0.5H), 7.4 (m, 7H), 6.95 (m, 2H), 5.00 (m, 1H), 4.91 (m, 1H) 4.80 (m, 0.5H), 4.55 (m, 0.5H), 4.28(m, 1H), 4.17 (m, 1H), 3.88 (dd, 1H, J=9, 14 Hz), 3.60 (m, 1H), 1.25 (s, 3H), 1.22 (s, 3H).

Provenance & Evidence