Hydrochloric Acid → 2-Acetylthio-3-(4-fluorophenyl)propionic acid

Temperature

-10 °C

Diphenylmethyl 2-acetylthio-3-(4-fluorophenyl)propionate (3.38 g, 8.27 mmol) was dissolved in anisole (9.0 ml), followed by cooling to -10° C. Into this solution was further dropped trifluoroacetic acid (51.0 ml). Next, this solution was heated to 0° C. About 1 hour thereafter, it was concentrated under reduced pressure. To the concentrate was added diethyl ether (80 ml) and the resulting solution was extracted with a saturated aqueous solution of sodium hydrogencarbonate (100 ml×2). To the alkaline aqueous solution thus obtained was added a 2N aqueous solution of hydrochloric acid until the solution became acidic. Further, it was extracted with methylene chloride (100 ml×3). The organic phase was washed with a saturated aqueous sodium chloride (100 ml) and dried over magnesium sulfate. After drying, the filtrate obtained by filtering thereof was concentrated under reduced pressure. Thus, the title compound (1.96 g, 98%) was obtained as colorless crystals.

1. temperatureNext, this solution was heated to 0° C
2. concentrationit was concentrated under reduced pressure
3. additionTo the concentrate was added diethyl ether (80 ml)
4. extractionthe resulting solution was extracted with a saturated aqueous solution of sodium hydrogencarbonate (100 ml×2)
5. customTo the alkaline aqueous solution thus obtained
6. extractionFurther, it was extracted with methylene chloride (100 ml×3)
7. washThe organic phase was washed with a saturated aqueous sodium chloride (100 ml)
8. dry with materialdried over magnesium sulfate
9. customAfter drying
10. customthe filtrate obtained
11. filtrationby filtering
12. concentrationthereof was concentrated under reduced pressure

ORD record

ord-d3581fcaa308430f8a8eafa9333a53ed

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05679671