تفاعل #2006414

معادلة التفاعل

NH4Cl

HCl

40

Methyl-4-(4-aminophenyl)-butanoate

Et3N

LiOH

benzenesulfonyl chloride

→

41

المردود 96.7%

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

المردود 96.7%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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

المصدر