Hydrochloric Acid → HCID 67040443, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Example 167C (117 mg, 0.156 mmol) in 1,4-dioxane (4 mL) was treated with a solution of lithium hydroxide monohydrate (13.1 mg, 0.312 mmol) in water (2 mL) at ambient temperature, then heated at 70° C. for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate (50 mL) and water (25 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 (58.5 mg, 71%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.34 (d, J=6.99 Hz, 6 H) 2.33 (s, 3 H) 3.14-3.30 (m, 1 H) 5.63 (s, 2 H) 6.65 (d, J=8.46 Hz, 2 H) 6.87 (s, 1 H) 6.91 (d, J=8.82 Hz, 1 H) 7.15 (d, J=8.46 Hz, 2 H) 7.65 (d, J=8.09 Hz, 1 H) 7.86 (d, J=7.72 Hz, 1 H) 8.03 (s, 1 H) 8.59 (s, 1 H) 8.89 (d, J=8.09 Hz, 1 H) 10.19 (s, 1 H) 12.17 (s, 1 H); MS (ESI+) m/z 528 (M+H)+, (ESI−) m/z 526 (M−H)−.

Provenance & Evidence