反応 #47833

反応方程式

triethylamine

cyclohexylamine

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid

6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic Acid

water

→

titled compound

収率 20.0%

6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic Acid Cyclohexylamide

収率 20.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他at 10° C
2. 2
   workup.STIRRINGstirred for additional 1 hr in a water bath
3. 3
   その他the reaction
4. 4
   洗浄the mixture washed with sodium bicarbonate
5. 5
   抽出extracted with dichloromethane
6. 6
   その他The organic layer was separated
7. 7
   乾燥dried over anhydrous MgSO4
8. 8
   濃縮concentrated under a reduced pressure
9. 9
   その他The resulting residue was purified by flash chromatography

実験手順

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid (100 mg, 0.38 mmol) obtained in Step 2 was dissolved in dichloromethane, and triethylamine (175 μl, 1.25 mmol) and cyclohexylamine (43 μl, 0.38 mmol) were added thereto at 10° C. Then, bis(2-oxo-3-oxazoline)phosphoryl chloride (100 mg, 0.38 mmol) was further added thereto, stirred for 10˜20 minutes at RT, and then stirred for additional 1 hr in a water bath. After water was added to complete the reaction, the mixture washed with sodium bicarbonate and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4, concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 26 mg of the titled compound (yield: 20.0%) as a red solid.

出典