Ethyl Acetate → (R)-5-(4-{1-ethyl-1-[4'-(1-hydroxy-1-methyl-ethyl)-2-methyl-biphenyl-4-yl]-propyl}-2-methyl-phenoxy)-4-hydroxy-pentanoic Acid

Temperature

75 °C

A 1.0 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.1 mL, 0.1 mmol) was added to a solution of (R)-5-(4-{1-ethyl-1-[2-methyl-4′-(1-methyl-1-trimethylsilanyloxy-ethyl)-biphenyl-4-yl]-propyl}-2-methyl-phenoxymethyl)-dihydro-furan-2-one (Example 15-(4); 16 mg, 0.028 mmol) in tetrahydrofuran (0.1 mL) at room temperature, and the mixture was stirred at 75° C. for two hours. Ethyl acetate was added to the reaction solution. The organic layer was washed with a potassium bisulfate aqueous solution and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (dichloromethane/methanol=10/1, developed three times) to give the title compound (11.3 mg, 78%).

1. washThe organic layer was washed with a potassium bisulfate aqueous solution and brine
2. dry with materialdried over anhydrous magnesium sulfate
3. distillationthe solvent was distilled off under reduced pressure
4. customThe residue was purified by silica gel chromatography (dichloromethane/methanol=10/1, developed three times)

ORD record

ord-3f045fa57b0041059493c17c9e219f73

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935688B2