HCID 15288589, compound → (Butyl((4-methylphenyl)sulfonyl)amino)acetic acid

HRID 1647695Notes

Reaction equation

HRID 1647695 reaction equation
[CH2:1]([N:5]([CH2:16][CH2:17][OH:18])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH2:2][CH2:3][CH3:4].CC(C)=[O:21].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([N:5]([CH2:16][C:17]([OH:21])=[O:18])[S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)(=[O:8])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 15288589HCID 15288589, compoundHCID 131709961Jones' reagent

Product 1

HCID 4177985(Butyl((4-methylphenyl)sulfonyl)amino)acetic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve N-butyl-N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide (10 mmol) in acetone (50 mL) and cool to 0° C. Add a slight excess of Jones reagent dropwise and allow the reaction to stir for 4 hours at 0° C. Add excess isopropanol and filter the reaction through a plug of diatomaceous earth. Rinse the plug with acetone (2×50 mL) and methylene chloride (3×50 mL). Combine the filtrates and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, methanol/methylene chloride) to provide [butyl-(toluene-4-sulfonyl)-amino]-acetic acid.

Workup

  1. customthe reaction
  2. filtrationAdd excess isopropanol and filter
  3. customthe reaction through a plug of diatomaceous earth
  4. washRinse the plug with acetone (2×50 mL) and methylene chloride (3×50 mL)
  5. concentrationCombine the filtrates and concentrate under vacuum
  6. customPurify the residue by flash chromatography (silica gel, methanol/methylene chloride)

Sources & evidence

ORD record
ord-c9359b5b70cd40229395e1c2d9106903
Source dataset
uspto-grants-1995_07
Patent number
US05434145

Reaction notes

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