Hydrochloric Acid → HCID 23579139, compound

Participants

Reaction Steps

To a solution of 3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-propionic acid methyl ester in 0.5 mL methanol and 0.3 mL tetrahydrofuran was added HCl (0.52 mL of a 4.0M solution in 1,4-dioxane, 2.09 mmol) and triethylsilane (0.134 mL, 0.84 mmol). The reaction mixture was stirred at room temperature for 24 hr. Saturated aqueous sodium bicarbonate was added and the aqueous solution was washed with methylene chloride. The organic layer was separated, dried (magnesium sulfate), and concentrated. Preparative thin layer chromatography afforded 0.059 g of 3-{4-[(3-hydroxy-benzyl)-(2,4,6-trimethyl-benzenesulfonyl)-amino]-phenyl}-propionic acid methyl ester. 1H NMR (CDCl3) δ 7.03 (t, 1H, J=8.0 Hz), 6.95–6.80 (m, 6H), 6.68–6.62 (m, 2H), 6.48 (bs, 1H), 4.69 (s, 2H), 3.59 (s, 3H), 2.81 (t, 2H, J=7.6 Hz), 2.51 (t, 2H, J=7.6 Hz), 2.41 (s, 6H), 2.24 (s, 3H).

Provenance & Evidence