Sodium Hydroxide → HCID 178446242, compound

Participants

Reaction Steps

A mixture of Example 10H (61 mg, 0.109 mmol) and 1.0 M sodium hydroxide (0.271 mL, 0.271 mmol) in ethanol (2 mL) was refluxed for 1 hour, cooled and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with 1% to 4% methanol in dichloromethane to give the title compound as a solid (26 mg, 47%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.55 (m, 1H) 0.83 (m, 6H) 0.88 (m, 1H) 0.99 (m, 2H) 1.26 (m, 1H) 1.38 (m, 1H) 1.61 (m, 1H) 2.38 (m, 1H) 3.12 (s, 3H) 3.45 (m, 2H) 3.63 (m, 1H) 3.73 (m, 1H) 3.99 (t, J=4.65 Hz, 2H) 7.05 (s, 1H) 7.24 (t, J=3.20 Hz, 1H) 7.40 (m, 2H) 7.83 (s, 1H) 8.00 (m, 2H); MS (ESI+) m/z 500 (M+H)+.

Provenance & Evidence