Hydrochloric Acid → HCID 86615555, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Example 161E (123.4 mg, 0.1558 mmol) in 1,4-dioxane (4 mL) was treated with a solution of lithium hydroxide monohydrate (13 mg, 0.3 116 mmol) in water (2 mL) at ambient temperature, then heated at 65° C. for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate (100 mL) and water (30 mL), adjusted the aqueous pH to 6 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 flash chromatography with 4% methanol/methylene chloride afforded the title compound (58 mg, 65%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.28 (s, 9 H) 1.34 (d, J=6.99 Hz, 6 H) 3.17-3.34 (m, 1 H) 5.64 (s, 2 H) 6.65 (d, J=8.46 Hz, 2 H) 6.80 (s, 1 H) 6.82 (d, J=8.46 Hz, 1 H) 7.16 (d, J=8.46 Hz, 2 H) 7.65 (d, J=8.46 Hz, 1 H) 7.88-7.98 (dd, 1 H) 8.11 (s, 1 H) 8.58 (s, 1 H) 8.89 (d, J=8.46 Hz, 1 H) 10.13 (s, 1 H) 12.47 (s, 1 H); MS (ESI+) m/z 570 (M+H)+, (ESI−) m/z 568 (M−H)−.

Provenance & Evidence