Boron tribromide → HCID 86668782, compound

Participants

Reaction Steps

Boron tribromide (750 ul, 0.75 mmol, 1.0 M in dichloromethane) was added to a solution of (+/−)-4-(4′-fluoro-3-methoxybiphenyl-4-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide prepared as in Example 18 (154 mg, 0.389 mmol) in dichloromethane (10 mL) at 0° C. The reaction was allowed to warm to rt and stirred until complete, then was diluted with water (60 mL) and extracted with ethyl acetate (3×60 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The solid was dissolved in 1N aqueous NaOH (60 mL), washed with ethyl acetate (3×80 mL), acidified using 1N aqueous HCl, and extracted with ethyl acetate (3×100 mL). The combined organics were dried (MgSO4), filtered, and concentrated in vacuo to afford the title compound as an off-white solid (25.4 mg, 17.1%). LC-MS m/z 382.5 (M+1). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.68 (s, 3H) 2.12-2.23 (m, 1H) 2.41-2.55 (m, 2H) 2.74-2.90 (m, 1H) 3.07 (s, 3H) 6.97-7.03 (m, 2H) 7.10-7.20 (m, 3H) 7.53-7.60 (m, 2H).

Provenance & Evidence