Gamma-Aminobutyric Acid → 4-[(phenylsulfonyl)amino]butanoic acid

HRID 1921663Notes

Reaction equation

HRID 1921663 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[OH-].[Na+]>[C:8]1([S:14]([NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 119Gamma-Aminobutyric AcidHCID 7369Benzenesulfonyl chloride

Product 1

HCID 3627414-[(phenylsulfonyl)amino]butanoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

7 G of gamma-aminobutyric acid was dissolved in 120 mL of 1N sodium hydroxide solution, and 15 g of benzenesulfonyl chloride was dropwise added thereto under ice-cooling. 2N sodium hydroxide solution was added to the mixture to adjust the pH to 9.2 and stirred for 4 hours. The stirred mixture was washed with 50 mL of ethyl acetate, and hydrochloric acid was added thereto to adjust the pH to 2 or less. After extracting with 500 mL of ethyl acetate, this was dried with magnesium sulfate and filtered. After a concentration under reduced pressure, the obtained residue was recrystallized with ethanol solution to give 13 g of the desired product.

Workup

  1. temperatureunder ice-cooling
  2. washThe stirred mixture was washed with 50 mL of ethyl acetate, and hydrochloric acid
  3. additionwas added
  4. extractionAfter extracting with 500 mL of ethyl acetate
  5. dry with materialthis was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationAfter a concentration under reduced pressure
  8. customthe obtained residue was recrystallized with ethanol solution

Sources & evidence

ORD record
ord-159bc24f5f5b4301b1ce38d4e2935c8c
Source dataset
uspto-grants-2012_05
Patent number
US08173705B2

Reaction notes

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