Methanol → 3-[Methyl(methylsulfonyl)amino]-5-(3-phenylpyrrolidin-1-yl)benzoic acid

To a solution of methyl 3-[methyl(methylsulfonyl)amino]-5-(2-oxo-4-phenylpyrrolidin-1-yl)benzoate obtained in Reference Example 18 0.20 g (0.50 mmol) in tetrahydrofuran (3 mL) was added 1.0 M BH3.tetrahydrofuran/tetrahydrofuran solution (1.5 mL) dropwise under ice-cooling and the mixture was stirred at room temperature for 16 hours. To the reaction solution was added methanol (3 mL) under ice-cooling, and the solvent was evaporated. The residue was dissolved in methanol (10 mL), and the mixture was stirred at 80° C. for 7 hours and the solvent was evaporated. The resulting solid was dissolved in a mixture of 2N aqueous sodium hydroxide solution (0.5 mL), methanol (0.5 mL) and tetrahydrofuran (0.5 mL) and the mixture was stirred at room temperature for 15 hours. The solvent was concentrated and the residue was adjusted by adding 1N hydrochloric acid to pH=3 and the mixture was extracted with ethyl acetate. After drying of the mixture on magnesium sulfate, the solvent was evaporated to give 165 mg (0.176 mmol) of the title compound (yield: 88%).

1. additionwas added 1.0 M BH3
2. temperaturecooling
3. customthe solvent was evaporated
4. dissolutionThe residue was dissolved in methanol (10 mL)
5. stirringthe mixture was stirred at 80° C. for 7 hours
6. customthe solvent was evaporated
7. dissolutionThe resulting solid was dissolved in a mixture of 2N aqueous sodium hydroxide solution (0.5 mL), methanol (0.5 mL) and tetrahydrofuran (0.5 mL)
8. stirringthe mixture was stirred at room temperature for 15 hours
9. concentrationThe solvent was concentrated
10. additionby adding 1N hydrochloric acid to pH=3
11. extractionthe mixture was extracted with ethyl acetate
12. customAfter drying of the mixture on magnesium sulfate
13. customthe solvent was evaporated

ORD record

ord-a17565728efa44fd88c5a90681851f5b

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816387B2