Reaktion #1447088

Reaktionsgleichung

dicyclohexylcarbodiimide

water

N-Boc-D-Homophenylalanine

3-aminoquinoline

→

title compound

Ausbeute 178.0%

N-Boc-D-Homophenylalanine Quinoline-3-amide

Ausbeute 178.0%

Lösungsmittel

acetic acid

triethylamine

acetonitrile

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Waschenthe filtrate washed with 1M hydrochloric acid (25 mL), saturated solution of sodium bicarbonate (25 mL) and water (25 mL)
3. 3
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated to dryness

Vorschrift

A solution of N-Boc-D-Homophenylalanine (3.0 g, 10.7 mmol) in ethyl acetate (100 mL) was treated with 3-aminoquinoline (3.08 g, 21.4 mmol) followed by dicyclohexylcarbodiimide (2.31 g, 11.2 mmol). The reaction was stirred at 25° C. for 3 hr (HPLC monitoring RP-18, 250×4 mm, water:acetonitrile:triethylamine:acetic acid=500:500:0.6:1 (mL), UV detector, λ=254 nm), filtered and the filtrate washed with 1M hydrochloric acid (25 mL), saturated solution of sodium bicarbonate (25 mL) and water (25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to afford title compound (4.3 g) as white solid.

Quelle