Iodoethane → 2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-butyric acid hydrochloride salt

Temperatur

-78 °C

To a solution of (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-phenyl)-acetic acid (70 mg, 0.12 mmol) in dry THF (50 mL) was added lithium diisopropylamide (0.17 mL, 0.35 mmol) dropwise with cooling to −78° C. After the reaction mixture was stirred at −78° C. for an additional 1 h, iodoethane (40 μl) was added. The reaction was warmed to RT over 4 h followed by quenching with saturated ammonium chloride (10 mL). Solvent was removed and the residue was partitioned between water and ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel column chromatograph (EtOAc:Hexane/20:80) to give the title compound as an oil (37 mg, 50%). MS m/e 609.2 (M+H)+.

1. temperatureThe reaction was warmed to RT over 4 h
2. customby quenching with saturated ammonium chloride (10 mL)
3. customSolvent was removed
4. customthe residue was partitioned between water and ethyl acetate
5. washThe combined organic layers were washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under vacuum
8. customThe residue was purified by silica gel column chromatograph (EtOAc:Hexane/20:80)

ORD-Eintrag

ord-70b1817fb6094aa4954bcb3f403ee9b9

Quelldatensatz

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07560586B2