反応 #73016

反応方程式

Ethoxyacetyl chloride

tert-butyl 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclohexylcarbamate

Sodium hydroxide

→

tert-butyl 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexylcarbamate

収率 38.0%

溶媒

ethanol

water

反応条件

後処理

1. 1
   workup.ADDITIONthe resulting product was treated
2. 2
   その他After the solvent was removed
3. 3
   その他to yield an oil
4. 4
   温度the solution was heated
5. 5
   温度at reflux for 6 h
6. 6
   その他The volatiles were removed under reduced pressure
7. 7
   その他the resulting brown oil was partitioned between dichloromethane (500 mL) and water
8. 8
   乾燥The organic layer was dried over Na2SO4
9. 9
   ろ過filtered
10. 10
    濃縮concentrated under reduced pressure
11. 11
    その他to yield a brown oil
12. 12
    その他Purification by flash chromatography (silica gel, 30% ethyl acetate/hexanes)

実験手順

Ethoxyacetyl chloride (9.00 g, 73.4 mmol) was reacted with tert-butyl 1-{[(3-aminoquinolin-4-yl)amino]methyl}cyclohexylcarbamate (27.2 g, 73.4 mmol) according to the method described in Part E of Example 9 and the resulting product was treated according to the method described in Part E of Example 9. After the solvent was removed to yield an oil, the oil was dissolved in ethanol (300 mL) and water (30 mL). Sodium hydroxide (4.3 g, 108 mmol) was added and the solution was heated at reflux for 6 h. The volatiles were removed under reduced pressure and the resulting brown oil was partitioned between dichloromethane (500 mL) and water. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield a brown oil. Purification by flash chromatography (silica gel, 30% ethyl acetate/hexanes) provided tert-butyl 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexylcarbamate as a brown solid (11.9 g, 38%).

出典