Sodium Hydroxide → Benzoic Acid

Temperature

40 °C

To a solution of ethyl 4′-[2-[(tert-butoxycarbonyl)-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]-2-methoxy-1,1′-biphenyl-4-carboxylate (220 mg) in ethanol (2.0 ml) was added 1N aqueous sodium hydroxide solution (1.2 ml), and the mixture was stirred at 40° C. for 3 hours. The solvent was removed by evaporation, and the aqueous solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate (30 ml×2). The combined organic layers were washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give a benzoic acid product. To a solution of the product in tetrahydrofuran (1.5 ml) was added 4N hydrochloride in dioxane (1.0 ml), and the mixture was stirred at room temperature for 12 hours. The resultant solid was collected by filtration and dried to give 4′-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-ethyl]-2-methoxy-1,1′-biphenyl-4-carboxylic acid hydrochloride (83 mg).

1. customThe solvent was removed by evaporation
2. extractionextracted with ethyl acetate (30 ml×2)
3. washThe combined organic layers were washed with water and brine
4. dry with materialdried over magnesium sulfate
5. customevaporated under reduced pressure

ORD record

ord-0dc9e2845f89427097f4f584d81ed47a

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629366B2