Sodium Hydroxide → HCID 22660091, compound

Temperature

52.5 °C

To a solution of 1-[4-(methylsulfonyl)butyl]cyclopentane carboxylic acid methyl ester (18.8 mmol, 4.94 g) in a mixture of THF (38 mL) and methanol (38 mL) was added 1 N sodium hydroxide (38 mL). The mixture was heated to 50-55° C. for 15 h at which point TLC analysis of the reaction mixture indicated the absence of starting material and the mixture was allowed to cool to room temperature. The solvent was removed under vacuum and the residue was diluted with water (100 mL) and extracted with ether (2×50 mL) to remove any neutral impurities. Then, the basic aqueous layer was acidified with 1 N hydrochloric acid and the product was extracted with ethyl acetate (2×75 mL). The combined extracts were washed with brine solution and dried over anhydrous sodium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the residue was dried under high vacuum to afford 4.31 g (92%) of the title compound as a low melting white solid. LR MS (C11H20O4S): 249 (M+H).

1. temperatureto cool to room temperature
2. customThe solvent was removed under vacuum
3. additionthe residue was diluted with water (100 mL)
4. extractionextracted with ether (2×50 mL)
5. customto remove any neutral impurities
6. extractionthe product was extracted with ethyl acetate (2×75 mL)
7. washThe combined extracts were washed with brine solution
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationAfter filtration of the drying agent
10. concentrationthe solution was concentrated under vacuum
11. customthe residue was dried under high vacuum

ORD record

ord-07eea14cfb1c4b84b369b78028bec3a1

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06806365B2