Sodium Hydroxide → HCID 86615562, compound

Participants

Reaction Steps

The product of Example 358B (162 mg, 0.1527 mmol) was suspended in methanol (2 mL) and treated with 10% sodium hydroxide in methanol (2 mL), sonicated briefly to achieve dissolution, and stirred at room temperature for one hour. The solvent was removed by rotary evaporation in vacuo and the residue taken up in ethyl acetate (150 mL) and water (50 mL). The aqueous pH was adjusted to 5 with 1N aqueous hydrochloric acid and the layers separated. The organic phase was washed with water (50 mL) and brine (50 mL), then dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation. Purification by silica gel flash chromatography with a gradient of 8% to 10% methanol/methylene chloride afforded the title compound (137 mg, 0.140 mmol, 92%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 0.60 (s, 3 H) 0.81 (s, 3 H) 0.98 (d, J=5.88 Hz, 3 H) 1.12-2.52 (m, 24 H) 1.33 (d, J=6.99 Hz, 6 H) 3.12-3.31 (m, 2 H) 3.55-3.69 (m, 1 H) 3.75-3.87 (m, 1 H) 4.02 (d, J=3.31 Hz, 1 H) 4.13 (d, J=3.68 Hz, 1 H) 4.32 (d, J=4.41 Hz, 1 H) 6.89-7.05 (m, 1 H) 7.40 (d, J=8.46 Hz, 2 H) 7.57-7.66 (m, 1 H) 7.68 (d, J=8.46 Hz, 2 H) 7.81-7.95 (m, 1 H) 8.01-8.12 (m, 2 H) 8.16 (d, J=8.82 Hz, 1 H) 8.50 (d, J=2.57 Hz, 1 H) 8.53-8.67 (m, 1 H) 8.76-8.96 (m, 1 H) 10.09 (s, 1 H) 10.21 (br s, 1 H) 10.97 (br s, 1 H); MS (ESI+) m/z 977/979 (M+H)+.

Provenance & Evidence