Reacción #2006414

Ecuación de reacción

NH4Cl

HCl

40

Methyl-4-(4-aminophenyl)-butanoate

Et3N

LiOH

benzenesulfonyl chloride

→

41

Rendimiento 96.7%

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

Rendimiento 96.7%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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

Fuente