Acetic Anhydride → HCID 11712603, compound

Participants

Reaction Conditions

Reaction Steps

Acetic anhydride (1.00 mL; 10.59 mmol) was added dropwise to formic acid (5 mL) at 0° C. and the mixture was stirred for 30 min. 1 mL of this solution was then added to a solution of N-[3-(1,3-benzodioxol-5-yl)-1-({[4-(4-fluorophenyl)-1-piperazinyl]sulfonyl}methyl)-2-propynyl]hydroxylamine (150.0 mg; 0.34 mmol) in THF (3 mL) and formic acid (0.7 mL) and the mixture was stirred overnight. The reaction mixture was then evaporated to dryness, the residue dissolved in MeOH and heated at 60° C. for 3 h. The solution was allowed to cool down to rt and the precipitate obtained was filtered. It was redissolved in EtOAc and precipitated again in pentane, filtered and dried under reduced pressure to give the title compound (1) (80 mg, 50% yield) as a white solid. HPLC, Rt: 3.58 min (purity: 96.9%). LC/MS, M+(ESI): 476.3, M−(ESI): 474.3. 1H NMR (CDCl3) δ: 9.55 (s, 0.5H), 9.12 (s, 0.5H), 8.1 (m, 1H), 6.90-7.09 (m, 7H), 6.05 (s, 2H), 4.81 (s, 0.5H), 4.61 (s, 0.5H), 3.62 (m, 2H), 3.31 (m, 4H), 3.14 (m, 4H).

Provenance & Evidence