Acetic Acid → HCID 56654741, compound

Participants

Reaction Steps

The compound of Example 86 (60 mg) was dissolved in THF (2 mL) and Rieke Zn in THF was then added dropwise (2 mL of a 0.7N solution). The mixture was then sonicated for 5 minutes. LC-MS (THF+a few drops of acetic acid) shows about 50% conversion. Another 4 equivalents of Zn was added, and again 15 minutes sonication. LC-MS shows the reaction mixture is gone to about 90% conversion. About 200 μL of acetic acid was then added, the reaction mixture was stirred for 2 minutes, then filtered over celite. The solution was concentrated under vacuum and the remaining oil dissolved in ethyl acetate and washed with NaHCO3, then dried over MgSO4, filtered and concentrated in vacuum. The remaining oil is purified via reverse phase chromatography. Yield 55 mg. LC-MS confirms desired product [m/z 542]. NMR 400 MHz δ ppm: 7.78 (d, 2H), 7.67 (d, 2H), 7.66 (s, 2H), 4.99 (m, 1H), 4.71 (m, 1H), 4.53 (m, 1H), 4.39 (m, 1H), 4.10 (d, 1H), 3.71 (d, 1H), 1.45-1.39 (m, 1H), 1.10-1.06 (m, 2H), 0.91-0.86 (m, 2H).

Provenance & Evidence