反応 #2006414

反応方程式

NH4Cl

HCl

40

Methyl-4-(4-aminophenyl)-butanoate

Et3N

LiOH

benzenesulfonyl chloride

→

41

収率 96.7%

4-[4-(Benzenesulfonylamino)-phenyl]-butyric Acid

収率 96.7%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他The phases were separated
2. 2
   抽出the organic layer was extracted several times with CH2Cl2
3. 3
   乾燥The combined organic extracts were dried over (MgSO4)
4. 4
   その他then evaporated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in a solvent mixture of THF (25 mL) and water (25 mL)
6. 6
   温度The mixture was heated at 50° C. for 1 h
7. 7
   その他The phases were separated
8. 8
   抽出the aqueous layer was extracted several times with AcOEt
9. 9
   乾燥The combined organic extracts were dried over (MgSO4)
10. 10
    その他then evaporated
11. 11
    その他The crude was purified by flash chromatography

実験手順

To a solution of 40 (500 mg, 2.59 mmol) in CH2Cl2 at room temperature were added Et3N (901 μL, 6.48 mmol) followed by benzenesulfonyl chloride (661 μL, 5.18 mmol). The mixture was stirred overnight at room temperature then treated with a saturated aqueous solution of NH4Cl. The phases were separated and the organic layer was extracted several times with CH2Cl2. The combined organic extracts were dried over (MgSO4) then evaporated under reduced pressure. The residue was dissolved in a solvent mixture of THF (25 mL) and water (25 mL) then LiOH (1.08 g, 25.9 mmol) was added. The mixture was heated at 50° C. for 1 h then treated with HCl (1N) until pH2. The phases were separated and the aqueous layer was extracted several times with AcOEt. The combined organic extracts were dried over (MgSO4) then evaporated. The crude was purified by flash chromatography using CH2Cl2/MeOH (95:5) as solvent mixture yielding 41 (800 mg, 96%) as a white solid

出典