反应详情

A solution of 2-ethoxy-3-{4-[2-(1-heptyl-3-p-tolyl-ureido)-ethyl]-phenyl}-propionic acid methyl ester (40 mg, 0.083 mmol) and 1 M LiOH (0.25 mmol, 0.25 mL) in tetrahydrofuran (2 mL) was allowed to stir at room temperature for 16 hours. The solution was quenched by the addition of 2 N HCl until the solution had a pH<2. After dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×). The organic layers were combined, washed with 2 M HCl (2×), dried over anhydrous sodium sulfate, and concentrated to a crude oil. The crude oil was chromatographed on silica gel (2% methanol/methylene chloride gradient to 15% methanol/methylene chloride) to give 2-ethoxy-3-{4-[2-(1-heptyl-3-p-tolyl-ureido)-ethyl]-phenyl}-propionic acid as a white waxy-solid (32 mg, 82%).

1. customThe solution was quenched by the addition of 2 N HCl until the solution
2. extractionAfter dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×)
3. washwashed with 2 M HCl (2×)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated to a crude oil
6. customThe crude oil was chromatographed on silica gel (2% methanol/methylene chloride gradient to 15% methanol/methylene chloride)