Sulfuric Acid → HCID 67190550, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-3-cyclobutyl-N-((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2-(3-methyl-4-methylsulfanyl-phenyl)-propionamide (300 mg, 0.73 mmol) in dioxane (4 mL) was treated with a 9 N aqueous sulfuric acid solution (2 mL). The resulting solution was then heated at 110° C. for 16 h. The reaction was then cooled and diluted with water (75 mL) and extracted with a chloroform/methanol solution (3:2, 2×50 mL) and then concentrated. The resulting residue was then dissolved in methylene chloride and concentrated with silica gel (2 g) and purified on Biotage Flash chromatography system (40S column, silica gel, 80% ethyl acetate/hexanes) to afford (R)-3-cyclobutyl-2-(3-methyl-4-methylsulfanyl-phenyl)-propionic acid (148 mg, 77%): [α]30589=−48.3° (c=0.18, methylene chloride); EI-HRMS m/e calcd for C15H20O2S (M+) 264.1184, observed 264.1183; 1H NMR (300 MHz, DMSO-d6) δ 1.47-2.14 (m, 9H, CH and 4×CH2), 2.21 (s, 3H, ArCH3), 2.43 (s, 3H, SCH3), 3.30 (t, J=7.4 Hz, 1H, ArCHCO), 7.05-7.15 (m, 3H, Ar), 12.28 (s, 1H, CO2H).

Provenance & Evidence