Tetrahydrofuran → (2E)-3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(3-Fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}prop-2-enoic acid

2 N aqueous sodium hydroxide solution (0.36 mL, 0.72 mmol) was added to a solution of methyl (2E)-3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}prop-2-enoate (111 mg, 0.24 mmol), which had been obtained in Example 1 (1f), in mixture of tetrahydrofuran (0.72 mL) and methanol (0.72 mL), and stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure. The residue was added with water (10 mL), subsequently with 1N aqueous hydrogen chloride solution (0.72 mL), and extracted with ethyl acetate (10 mL×2). After that, the organic layers were combined, washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the title compound as a white amorphous substance (71 mg, yield 67%).

1. concentrationThe reaction solution was concentrated under reduced pressure
2. additionThe residue was added with water (10 mL), subsequently with 1N aqueous hydrogen chloride solution (0.72 mL)
3. extractionextracted with ethyl acetate (10 mL×2)
4. washwashed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure

ORD record

ord-a560ecd37586488e84573e979ff7f1ae

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173631B2