Hydrochloric Acid → 4-[4-(Benzenesulfonylamino)-phenyl]-butyric acid

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

1. customThe phases were separated
2. extractionthe organic layer was extracted several times with CH2Cl2
3. dry with materialThe combined organic extracts were dried over (MgSO4)
4. customthen evaporated under reduced pressure
5. dissolutionThe residue was dissolved in a solvent mixture of THF (25 mL) and water (25 mL)
6. temperatureThe mixture was heated at 50° C. for 1 h
7. customThe phases were separated
8. extractionthe aqueous layer was extracted several times with AcOEt
9. dry with materialThe combined organic extracts were dried over (MgSO4)
10. customthen evaporated
11. customThe crude was purified by flash chromatography

ORDレコード

ord-c372fef9087f447b9b2ffcc98699279c

出典データセット

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06541661B1