Hydrochloric Acid → HCID 67040972, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Example 231E (96 mg, 0.1187 mmol) in 1,4-dioxane (2 mL) was treated with a solution of lithium hydroxide monohydrate (10.0 mg, 0.2374 mmol) in water (1 mL) at ambient temperature, then heated at 70° C. for 30 minutes. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL) and water (30 mL), adjusted the aqueous pH to 5 with 1N aqueous hydrochloric acid, and separated the layers. The organic phase was washed with water (2×25 mL) and brine (25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation in vacuo. Purification of the residue by silica gel chromatography eluting with 5% methanol/methylene chloride afforded the title compound as a light yellow solid (36 mg, 2%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (d, J=6.62 Hz, 6 H) 3.12-3.30 (m, 1 H) 5.61 (s, 2 H) 6.64 (d, J=8.09 Hz, 2 H) 6.90 (dd, J=6.43, 1.29 Hz, 1 H) 7.15 (d, J=8.46 Hz, 2 H) 7.65 (dd, J=8.09, 1.84 Hz, 1 H) 7.81 (dd, J=7.91, 2.39 Hz, 1 H) 7.97 (s, 1 H) 8.43 (d, J=1.84 Hz, 1 H) 8.48-8.51 (m, 2 H) 8.59 (s, 1 H) 8.88 (d, J=1.84 Hz, 1 H) 10.18 (s, 1 H) 10.51 (s, 1 H); MS (ESI+) m/z 586/588 (M+H)+.

Provenance & Evidence