Réaction #2006414

Équation de réaction

NH4Cl

HCl

40

Methyl-4-(4-aminophenyl)-butanoate

Et3N

LiOH

benzenesulfonyl chloride

→

41

Rendement 96.7%

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

Rendement 96.7%

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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

Source