Sodium Hydroxide → HCID 57708946, compound

Participants

Reaction Steps

A sodium hydroxide aqueous solution (1 M, 0.5 mL, 0.5 mmol) was added to a mixture of 3-[4′-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2′-methyl-biphenyl-4-yl]-propionic acid methyl ester (Example 11-(3); 0.013 g, 0.02 mmol), tetrahydrofuran (0.5 mL) and methanol (1.0 mL) while stirring at room temperature, and the mixture was stirred at the same temperature for two hours. A 30% sodium dihydrogenphosphate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Tetra-n-butylammonium fluoride (1 M solution in tetrahydrofuran, 0.1 mL, 0.1 mmol) and tetrahydrofuran (1 mL) were added to the resulting residue, and the mixture was stirred at 60° C. for four hours. A 30% sodium dihydrogenphosphate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a 30% sodium dihydrogenphosphate aqueous solution and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (dichloromethane/methanol=10/1) to give the title compound (0.007 g, 67%).

Provenance & Evidence