Tetrahydrofuran → 4-{[Cyclopentyl(3-methyl-1-benzothiophen-2-yl)methyl]amino}benzoic acid

To a mixture of methyl 4-{[cyclopentyl(3-methyl-1-benzothiophen-2-yl)methyl]amino}benzoate (1.56 g) synthesized above, tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1N aqueous sodium hydroxide solution (20.0 mL), and the mixture was stirred with heating under reflux for 4 hr, and concentrated under reduced pressure. The residue was dissolved in water (40 mL), and 1N hydrochloric acid (20.0 mL) was added at 0° C. The resulting precipitate was collected by filtration, and the obtained pale-brown solid was dissolved in ethyl acetate. The solution was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (1.42 g, 95%) as a pale-brown solid.

1. temperaturewith heating
2. temperatureunder reflux for 4 hr
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in water (40 mL)
5. addition1N hydrochloric acid (20.0 mL) was added at 0° C
6. filtrationThe resulting precipitate was collected by filtration
7. dissolutionthe obtained pale-brown solid was dissolved in ethyl acetate
8. washThe solution was washed with saturated brine
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-3d725fd01a0e4b089e9a4adc9cc7bd4a

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2