Réaction #1447088

Équation de réaction

dicyclohexylcarbodiimide

water

N-Boc-D-Homophenylalanine

3-aminoquinoline

→

title compound

Rendement 178.0%

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

Rendement 178.0%

Solvants

acetic acid

triethylamine

acetonitrile

ethyl acetate

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source