Oxalyl chloride → HCID 22262076, Verbindung

To a solution of 8-bromo-1-naphthalenecarboxylic acid (161 mg, 0.64-mmol) in tetrahydrofuran (5 ml) were added oxalyl chloride (0.11 ml, 1.72 mmol) and N,N-dimethylformamide (0.01 ml), and the mixture was stirred at room temperature for 30 min. The reaction solution was evaporated under reduced pressure. To a solution of the residue in ethyl acetate (5 ml). were added (1RS,2SR)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride (150 mg, 0.43 mmol) and saturated aqueous sodium hydrogen carbonate (5 ml) and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (50 ml) and extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1). Recrystallization from ethyl acetate-hexane gave the title compound (67 mg, 29%).

1. customThe reaction solution was evaporated under reduced pressure
2. stirringthe mixture was stirred overnight at room temperature
3. extractionextracted with ethyl acetate (50 ml×2)
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customevaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1)
8. customRecrystallization from ethyl acetate-hexane

ORD-Eintrag

ord-0597b4035a6343dc8674a5202d07984b

Quelldatensatz

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06982348B2