Tetrabutylammonium Fluoride → HCID 57504508, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (1M in THF) (2028 μl, 2.03 mmol) was added to (S)-2-(tert-butyldimethylsilyloxy)-3-((S)-1-methoxypropan-2-yloxy)-N-(5-methylpyridin-2-yl)propanamide (Intermediate Y4) (388 mg, 1.01 mmol) in THF (5 mL) at 20° C. The resulting solution was stirred at room temperature for 3 hours. The reaction mixture was concentrated, diluted with ethyl acetate (50 mL), and washed sequentially with water (25 mL) and saturated brine (10 mL). The organic layer was dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 10% s MeOH in DCM to afford the product (200 mg, 74%). 1H NMR (400 MHz, DMSO) δ 1.04 (d, 3H), 2.24 (s, 3H), 3.17-3.23 (m, 4H), 3.25-3.31 (m, 1H), 3.55-3.73 (m, 3H), 4.16-4.23 (m, 1H), 5.94 (d, 1H), 7.59-7.65 (m, 1H), 7.98 (d, 1H), 8.12-8.16 (m, 1H), 9.48 (s, 1H); m/z (ESI+) (M+H)+=269.31; HPLC tR=1.11 min.

Provenance & Evidence