Hydrochloric Acid → HCID 87113395, compound

Participants

Reaction Steps

A mixture of Example 52D (1.59 g, 4.94 mmol) and oxalic acid (0.71 g, 7.9 mmol) in THF (16 mL)/water (8 mL) was stirred at ambient temperature for 2 hr. Additional oxalic acid (0.71 g, 7.9 mmol) and THF (16 mL) were added and the reaction mixture was stirred for 2 additional hr. HCl (4 N in dioxane, 5 mL) was then added and the reaction mixture was stirred 16 hr at ambient temperature, and then quenched by addition of saturated aq Na2CO3 solution (10 mL). The mixture was partitioned between Et2O and H2O, and the separated aqueous phase was extracted with Et2O. The combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified on silica gel (Analogix® Intelliflash 280™; SF25-120 g column; 100% hexane 7 min, then 0% to 20% EtOAc/hexanes eluant, 23 min) which yielded 1.13 g (83%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.98 (s, 1H), 8.27-8.21 (m, 2H), 7.97 (dd, J=9.0, 0.6, 2H). MS (DCI+) m/z 293 (M+NH4).

Provenance & Evidence