Hydrochloric Acid → HCID 86707742, compound

Participants

Reaction Steps

To a solution of Compound 181b (41 mg, 0.070 mmol) in THF (3 mL) at 0° C. was slowly added a solution of 25% NaOMe in MeOH (0.035 mL, 0.15 mmol) dissolved in THF (0.5 mL) and the mixture was stirred for 30 min. The reaction was quenched with the addition of cold 1.0 M HCl (0.70 mL, 0.70 mmol) at 0° C., then the mixture was extracted with DCM. The extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-100% EtOAc/hexanes to give Compound 181c (12 mg, 36% yield) as a yellow foam. 1H NMR (400 MHz, CDCl3) δ 8.08-8.03 (m, 2H), 7.73 (dd, J=8.6, 1.8 Hz, 1H), 7.66-7.59 (m, 2H), 7.51-7.43 (m, 2H), 7.42-7.35 (m, 1H), 4.73 (s, 2H), 4.69 (dd, J=9.0, 3.5 Hz, 1H), 3.54 (dd, J=16.8, 3.6 Hz, 1H), 3.41-3.30 (m, 1H), 2.70 (dt, J=7.1, 3.4 Hz, 1H), 1.21-1.05 (m, 2H), 1.04-0.86 (m, 2H). LCMS=1.9 min using analytical method (M), 482.0 (M+H)+.

Provenance & Evidence