반응 #2006414

반응 방정식

NH4Cl

HCl

40

Methyl-4-(4-aminophenyl)-butanoate

Et3N

LiOH

benzenesulfonyl chloride

→

41

수율 96.7%

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

수율 96.7%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타The phases were separated
2. 2
   추출the organic layer was extracted several times with CH2Cl2
3. 3
   건조The combined organic extracts were dried over (MgSO4)
4. 4
   기타then 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
   온도The mixture was heated at 50° C. for 1 h
7. 7
   기타The phases were separated
8. 8
   추출the aqueous layer was extracted several times with AcOEt
9. 9
   건조The combined organic extracts were dried over (MgSO4)
10. 10
    기타then evaporated
11. 11
    기타The crude was purified by flash chromatography

실험 절차

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

출처