Reaktion #661439

Reaktionsgleichung

3-((R)-2-amino-2-phenyl-ethyl)-1-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-5-[4-(3-nitro-benzyl)-piperazin-1-yl]-1H-pyrimidine-2,4-dione

N,N-diisopropylethylamine

4-bromo-butyric acid ethyl ester

→

compound

Ausbeute 33.0%

4-((R)-2-{3-(2-Fluoro-6-trifluoromethyl-benzyl)-4-methyl-5-[4-(3-nitro-benzyl)-piperazin-1-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl}-1-phenyl-ethylamino)-butyric acid ethyl ester

Ausbeute 33.0%

Lösungsmittel

acetonitrile

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled to room temperature
2. 2
   Waschenwashed with an aqueous saturated sodium bicarbonate solution
3. 3
   SonstigeThe organic layer thus formed
4. 4
   Sonstigewas separated
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified
7. 7
   Sonstigedried in a vacuum

Vorschrift

To a solution of 3-((R)-2-amino-2-phenyl-ethyl)-1-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-5-[4-(3-nitro-benzyl)-piperazin-1-yl]-1H-pyrimidine-2,4-dione (3-58) (55 mg, 0.086 mmol) in acetonitrile (2 mL) were added N,N-diisopropylethylamine (37 μl, 0.271 mmol) and 4-bromo-butyric acid ethyl ester (15 μl, 0.086 mmol) in the order, followed by stirring at 95° C. for 12 hrs. The solution was cooled to room temperature, diluted with dichloromethane and washed with an aqueous saturated sodium bicarbonate solution. The organic layer thus formed was separated and concentrated. The residue was purified using silica gel chromatography (eluent: dichloromethane/methanol, 30/1) and dried in a vacuum to afford 21 mg of the compound as a colorless oil (yield 33%). 1H NMR (300 MHz, CDCl3) δ 1.19 (3H, t), 1.65 (2H, m), 2.24 (4H, m), 2.33 (3H, s), 2.37-2.50 (4H, m), 2.74 (2H, m), 3.60 (4H, m), 4.02-4.09 (4H, m), 4.16 (1H, m), 5.40 (2H, dd), 7.20-7.40 (7H, m), 7.49 (1H, t), 7.53 (1H, d), 7.76 (1H, d), 8.10 (1H, dd), 8.18 (1H, s)

Quelle