Sodium Hydroxide → HCID 90413704, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 219B (350 mg, 0.887 mmol) in 10 mL dioxane was added 6M aqueous sodium hydroxide (1.479 mL, 8.87 mmol). The mixture was heated at 50° C. for 12 hours, cooled and diluted with 25 mL water. The basic aqueous layer was extracted with ethyl acetate (twice) and the organics were discarded. To the basic aqueous layer was added 25 mL ethyl acetate and the aqueous layer made slightly acidic with 2.5M hydrochloric acid. The aqueous layer was extracted with ethyl acetate (twice) and the combined organics were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.60-1.77 (m, 1H) 1.99-2.12 (m, 1H) 2.28-2.46 (m, 3H) 2.53 (dd, J=7.78, 2.90 Hz, 2H) 3.62-3.89 (m, 3H) 6.18 (d, J=1.83 Hz, 1H) 6.53 (s, 1H) 7.02 (d, J=4.88 Hz, 1H) 7.08-7.42 (m, 3H) 8.17 (d, J=4.88 Hz, 1H) 11.73 (d, J=1.53 Hz, 1H) 11.96-12.37 (m, J=2.44 Hz, 1H); MS (ESI): 367.2 (M+H)+.

Provenance & Evidence