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

HRID 2402413Notes

Reaction equation

HRID 2402413 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1.CCN(CC)CC.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[NH4+].[Cl-].[Li+].[OH-].Cl>C(Cl)Cl>[C:22]1([S:28]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][CH2:4][C:3]([OH:2])=[O:14])=[CH:8][CH:9]=2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 88628Methyl 4-aminobenzenebutanoate

Product 1

HCID 98400354-[4-(Benzenesulfonylamino)-phenyl]-butyric acidYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 40 (500 mg, 2.59 mmol) in CH2Cl2 at room temperature were added Et3N (901 μμL, 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

Workup

  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

Sources & evidence

ORD record
ord-05d6521f7d86499f8ba54665b032f44d
Source dataset
uspto-grants-2014_08
Patent number
US08796330B2

Reaction notes

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