Trifluoroacetic acid → HCID 9816269, Verbindung

Temperatur

2.5 °C

Under a nitrogen atmosphere, a cold (0-5° C.), stirring solution of (4E)-N-methyl-N-(tert-butoxycarbonyl)-5-(3,4-dichlorophenyl)-4-penten-2-amine (1.38 g, 4.01 mmol) in anisole (20 mL) was treated drop-wise over 45 min with trifluoroacetic acid (20.72 g, 181.7 mmol). The resulting solution was stirred for 1.5 h at 0-5° C. The solution was then concentrated by rotary evaporation followed by further drying under high vacuum. The resulting residue was cooled (0-5° C.), basified with 10% NaOH solution (15 mL), treated with saturated NaCl solution (10 mL) and extracted with CHCl3 (6×20 mL). The combined CHCl3 extracts were washed with saturated NaCl solution (25 mL), dried (Na2SO4), filtered, concentrated by rotary evaporation, followed by further drying under high vacuum to produce a light-brown oil (0.96 g). The crude product was purified by column chromatography on silica gel (50 g), eluting with CH3OH—Et3N (98:2, v/v). Selected fractions containing the product (Rf 0.44) were combined and concentrated on a rotary evaporator. The residue was dissolved in CHCl3. The CHCl3 solution was dried (Na2SO4), filtered, concentrated by rotary evaporation and dried under high vacuum to give 467 mg (47.7%) of a light-yellow oil.

1. concentrationThe solution was then concentrated by rotary evaporation
2. customby further drying under high vacuum
3. temperatureThe resulting residue was cooled (0-5° C.)
4. additiontreated with saturated NaCl solution (10 mL)
5. extractionextracted with CHCl3 (6×20 mL)
6. washThe combined CHCl3 extracts were washed with saturated NaCl solution (25 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated by rotary evaporation
10. customby further drying under high vacuum

ORD-Eintrag

ord-89cbb6c548b049c09ca6f631548a507f

Quelldatensatz

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06337351B1