Acetic-formic anhydride → HCID 11588997, compound

Participants

Reaction Steps

To a solution of 1-{[2-(hydroxyamino)hept-3-yn-1-yl]sulfonyl}-4-pyridin-2-ylpiperazine (157 mg; 0.45 mmol) in THF (5 mL) was added a solution of acetyl formate (200 mg, prepared as described by Kolle et al., 1983, Helvetica Chimica Acta, 66(8), 2760-8) in THF (2 mL). The reaction mixture was stirred at rt for 5 h and concentrated under reduced pressure. Purification of the crude by flash chromatography on silica (EtOAc:c-Hex, gradient from 50:50 to 100:0) gave the title compound as a white foam (90 mg, 53% yield). HPLC, Rt: 3.04 min (purity: 97.9%). LC/MS, M+(ESI): 381.3, M−(ESI): 379.2. 1H NMR (DMSO-d6) δ: 8.39 (brs, 0.4H), 8.18 (m, 1H), 8.08 (brs, 0.6H), 7.48 (m, 1H), 6.66 (m, 2H), 5.53 (brs, 0.4H), 5.01 (brs, 0.6H), 3.63 (m, 5H), 3.36 (m, 6H), 2.14 (m, 2H), 1.49 (sx, J=7.2 Hz, 2H), 0.93 (t, J=7.3 Hz, 3H).

Provenance & Evidence