反応 #1509621

反応方程式

EDC HOBt

2-amino-4-(3-carboxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester

1-hydroxybenzotriazole

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

→

2-amino-4-[3-(pyrimidin-2-ylcarbamoyl)-propyl]-imidazole-1-carboxylic acid tert-butyl ester

溶媒

DMF

反応条件

後処理

1. 1
   濃縮The reaction was concentrated under reduced pressure
2. 2
   その他the residue partitioned between ethyl acetate (20 mL) and water (10 mL) The organic layer
3. 3
   洗浄was successively washed with water (3×10 mL)
4. 4
   乾燥a 10% aqueous solution of citric acid (2×10 mL), sat. NaHCO3 (2×10 mL), and brine (10 mL) before being dried (Na2SO4)
5. 5
   その他evaporated to dryness
6. 6
   その他The crude product was purified via flash column chromatography (2-10% MeOH/CH2Cl2)
7. 7
   その他to afford the target compound

実験手順

General EDC/HOBt Procedure: 2-amino-4-(3-carboxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester 22 (100 mg, 0.371 mmol), 1-hydroxybenzotriazole (100 mg, 0.742 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (142 mg, 0.742 mmol) were dissolved in anhydrous DMF (3 mL). The appropriate amine coupling partner (1.48 mmol) was then added and the solution was stirred at ambient temperature until completion was evident by TLC analysis. The reaction was concentrated under reduced pressure and the residue partitioned between ethyl acetate (20 mL) and water (10 mL) The organic layer was successively washed with water (3×10 mL), a 10% aqueous solution of citric acid (2×10 mL), sat. NaHCO3 (2×10 mL), and brine (10 mL) before being dried (Na2SO4) and evaporated to dryness. The crude product was purified via flash column chromatography (2-10% MeOH/CH2Cl2) to afford the target compound.

出典