Reaktion #1521

ord-679c764250d94da2b08939ad59ce9559

Reaktionsgleichung

CCCCCC[C@@H](OC(=O)c1ccc(C(=O)OCc2ccccc2)cc1)C(F)(F)F
4-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid benzyl ester
[H][H]
hydrogen
CCCCCC[C@@H](OC(=O)c1ccc(C(=O)O)cc1)C(F)(F)F
4-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid
Ausbeute 98.9%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstige5% palladium/carbon was removed
  2. 2
    Einengenthe filtrate was concentrated
  3. 3
    SonstigeThe concentrate obtained
  4. 4
    Sonstigewas purified by column chromatography

Vorschrift

Then, 0.07 g of 5% palladium/carbon and 10 ml of a tetrahydrofuran solution containing 0.63 g of 4-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid benzyl ester were stirred overnight at room temperature in a stream of hydrogen to decompose a benzyl protective group by hydrogenation. 5% palladium/carbon was removed using Celite as a filter aid, and the filtrate was concentrated. The concentrate obtained was purified by column chromatography to obtain 0.49 g of 4-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid as a colorless liquid (gradually crystallized) (isolated yield: 98%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05725798uspto-grants-1998_03