Reaktion #2006414

Reaktionsgleichung

NH4Cl

HCl

40

Methyl-4-(4-aminophenyl)-butanoate

Et3N

LiOH

benzenesulfonyl chloride

→

41

Ausbeute 96.7%

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

Ausbeute 96.7%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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

Quelle