Acetohydroxamic Acid → HCID 178475149, compound

Participants

Reaction Steps

To a mixture of Example 1A (150 mg, 0.35 mmol) and N-hydroxyacetamide (52.3 mg, 0.70 mmol) in THF (10 mL) was added sodium tert-butoxide (67.0 mg, 0.70 mmol). The mixture was stirred at room temperature for 6 hours. The reaction mixture was diluted with ether and washed with brine. The aqueous phase was extracted with ether (2×20 mL), dried over MgSO4, and filtered. The mixture was concentrated under reduced pressure and the residue was purified by FC on SiO2 using an Analogix® Intelliflash280™ (eluted with Hexanes-EtOAc: 0-30%) to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.19 (s, 9 H), 1.21 (m, 1 H), 1.37 (s, 1 H), 1.94 (s, 2 H), 1.97-2.11 (m, 1 H), 3.65-3.92 (m, 2 H), 3.99-4.33 (m, 2 H), 4.34-4.55 (m, 1 H), 6.82 (s, 1 H), 7.66 (dd, J=9.2, 2.4 Hz, 1 H), 8.34 (d, J=8.8 Hz, 1 H), 8.61 (d, J=2.4 Hz, 1 H); MS (ESI) m/z 486 (M+H)+.

Provenance & Evidence