Hydrochloric Acid → HCID 68872790, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 157C (1.06 g, 4.10 mmol) in dioxane (10 mL) was added 1 N NaOH (10 mL, 10 mmol) and the reaction mixture heated at 95° C. for 16 hours. After cooling the solution to room temperature, the reaction mixture was diluted with 50 mL of water, the pH adjusted to 2.0 with 1N HCl, and the aqueous layer extracted 3 times with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. The product was purified by flash chromatography on SiO2 eluting with a 10-25% ethyl acetate/hexane gradient yielding the title compound (0.635 g, 64% yield) as a crystalline solid. 1H NMR (300 MHz, DMSO-d6): δ ppm−0.51 (m, 2H) −0.02 (m, 2H) 0.14 (m, 2H) 0.46 (m, 1H) 1.16 (s, 3H) 5.42 (s, 1H) 7.12 (t, J=7.35 Hz, 1H) 7.34 (m, 2H) 7.64 (d, J=7.35 Hz, 1H). MS (ESI+) m/z=243 (M+H)+.

Provenance & Evidence