Hydrochloric Acid → HCID 18189440, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 35A (77 mg, 0.210 mmol) in THF (5 mL) at 0° C. was treated with bistrimethylsilylacetamide (52 μL, 0.210 mmol), stirred for 1 hour, and concentrated. The concentrate was dissolved in THF (5 mL), cooled to 0° C., treated with 1M potassium tert-butoxide (210 μL, 0.210 mmol), stirred for 1 hour, treated with ethyl iodide (17 μL, 0.210 mmol), stirred at room temperature for 72 hours, treated with 1M HCl (5 mL), stirred for 2 hours, poured into saturated NaHCO3, and extracted with ethyl acetate. The extract was washed with brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by reverse-phase HPLC with CH3CN/water to provide the desired product as the fraction which eluted at 25 minutes. MS (ESI(−)Q1MS) m/z 394 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ9.84 (br s, 1H), 8.43-8.41 (d, J=8.7 Hz, 1H), 7.37-7.23 (m, 6H), 7.14-7.10 (t, J=8.0 Hz, 1H), 6.89 (d, J=2.4 Hz, 1H), 6.71-6.69 (dd, J=7.6, 0.7 Hz ,1H), 6.63-6.60 (dd, J=7.3, 1.0 Hz ,1H), 6.20 (s, 1H), 4.16-4.09 (m, 2H), 3.00 (s, 3H), 1.46-1.42 (t, J=6.9, 3H).

Provenance & Evidence