Potassium Hydroxide → (Cyclopentylsulfanyl)acetic acid

A solution of 20% aqueous KOH (14.8 g, 52.8 mmol) was added to a solution of the product from Example 143A (8.89 g, 46.7 mmol) in EtOH (30 mL), and the resulting mixture was heated at reflux for 3 hours. The reaction solution was cooled to room temperature and concentrated under vacuum. The residue was diluted with water (20 mL) and CH2Cl2 (50 mL) and cooled in ice as 37% HCl (15 mL) was added gradually with good stirring (final pH˜2). The aqueous layer was separated and extracted with CH2Cl2 (50 mL) and the combined organic phase was washed with brine (30 mL), dried (Na2SO4), filtered, and concentrated under vacuum to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.44-1.66 (m, 4H), 1.67-1.86 (m, 2H), 1.93-2.12 (m, 2H), 3.14-3.31 (m, 1H), 3.30 (s, 2H).

1. temperaturethe resulting mixture was heated
2. temperatureat reflux for 3 hours
3. concentrationconcentrated under vacuum
4. additionThe residue was diluted with water (20 mL) and CH2Cl2 (50 mL)
5. temperaturecooled in ice as 37% HCl (15 mL)
6. additionwas added gradually
7. customThe aqueous layer was separated
8. extractionextracted with CH2Cl2 (50 mL)
9. washthe combined organic phase was washed with brine (30 mL)
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated under vacuum

ORD record

ord-bb76f99c475a4339bef6698d4374b6b6

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609669B2