Reaction #1447088

Reaction equation

dicyclohexylcarbodiimide

water

N-Boc-D-Homophenylalanine

3-aminoquinoline

→

title compound

Yield 178.0%

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

Yield 178.0%

Solvents

acetic acid

triethylamine

acetonitrile

ethyl acetate

Conditions

Workup

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

Procedure

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