Sodium Hydroxide → 2-{Benzyl[(4-methoxyphenyl)sulfonyl]amino}acetic acid

HRID 1393846Notes

Reaction equation

HRID 1393846 reaction equation
[CH2:1]([N:8]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH2:9][C:10]([O:12]CC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([N:8]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH2:9][C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3503631Ethyl 2-[[4-methoxybenzenesulfonyl](benzyl)amino]acetate

Product 1

HCID 7188402-{Benzyl[(4-methoxyphenyl)sulfonyl]amino}acetic acidYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-{benzyl[(4-methoxyphenyl)sulfonyl]amino}acetate (11.62 g, 31.97 mmol) was dissolved in ethanol (100 ml), and 1N sodium hydroxide (100 ml) was added thereto. After being reacted for 16 hours at room temperature, the solvent was evaporated out. 3N hydrochloric acid (150 ml) was added to the residue and the water phase was extracted with ethyl acetate (200 ml×2). The organic layer was washed with saturated brine, and then dried over sodium sulfate. The solvent was evaporated out and the residue was purified by silica gel column chromatography (chloroform:methanol=10:1), to give 2-{benzyl[(4-methoxyphenyl)sulfonyl]amino}acetic acid (10.57 g, 99%).

Workup

  1. customAfter being reacted for 16 hours at room temperature
  2. customthe solvent was evaporated out
  3. addition3N hydrochloric acid (150 ml) was added to the residue
  4. extractionthe water phase was extracted with ethyl acetate (200 ml×2)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated out
  8. customthe residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-a6c8ecb0d5a04856b1e5d16e3377e958
Source dataset
uspto-grants-2008_03
Patent number
US07348017B2

Reaction notes

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