HCID 71117412, compound → HCID 71139024, compound

Temperature

70 °C

Eaton's reagent (100 mL, 630 mmol, 6.6 equiv.) was added to 2-[(3-fluorophenyl)amino]cyclopentanecarboxylic acid 6A (21.3 g, 95 mmol, 1 equiv). The mixture was heated to 70° C. and stirred for one hour. The reaction mixture was then cooled to 23° C. and quenched with the addition of wet ice. The mixture was then neutralized to pH=10 with the portionwise addition of solid sodium hydroxide pellets. The reaction mixture was then partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The filtrate was purified by flash-column chromatography (hexanes, grading to 50% ethyl acetate-hexanes) to afford 6B. [M+H]+: 206.2.

1. temperatureThe reaction mixture was then cooled to 23° C.
2. customquenched with the addition of wet ice
3. additionThe mixture was then neutralized to pH=10 with the portionwise addition of solid sodium hydroxide pellets
4. customThe reaction mixture was then partitioned between ethyl acetate and water
5. washThe organic layer was washed with saturated aqueous sodium chloride solution
6. dry with materialthe washed solution was dried over sodium sulfate
7. filtrationThe dried solution was filtered
8. concentrationthe filtrate was concentrated
9. customThe filtrate was purified by flash-column chromatography (hexanes, grading to 50% ethyl acetate-hexanes)

ORD record

ord-9c01825ee0ea41f7b2d5525185b9409a

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592383B2