Lithium Hydroxide → 2-(Benzyloxy)-5-(pyridin-4-yl)benzoic acid

Solid LiOH (0.79 g, 18.77 mmol) was added to a stirred solution of phenylmethyl 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoate (may be prepared as described in Description 78; 0.81 g, 1.88 mmol) in tetrahydrofuran (50 ml) and water (10 ml) in air at room temperature. The reaction mixture was stirred at 70° C. overnight. After the reaction mixture was cooled to room temperature, the solvent was removed and the residue was dissolved in water (100 ml) and stirred in an ice-water bath. 1N HCl (aq) was added to adjust the pH to 4. The solid was filtered, and dissolved in ethyl acetate (80 ml). The solution was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield the title compound as a white solid, 486 mg.

1. temperatureAfter the reaction mixture was cooled to room temperature
2. customthe solvent was removed
3. dissolutionthe residue was dissolved in water (100 ml)
4. stirringstirred in an ice-water bath
5. addition1N HCl (aq) was added
6. filtrationThe solid was filtered
7. dissolutiondissolved in ethyl acetate (80 ml)
8. dry with materialThe solution was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-fdc2c724d0c74639be7264bc26f17f5b

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08778939B2