Sodium Hydroxide → {2-[(4-methoxy-2,6-dimethyl-benzenesulfonyl)-methyl-amino]-ethoxy}acetic Acid

HRID 2388657Notes

Reaction equation

HRID 2388657 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][CH2:16][O:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][CH2:16][O:17][CH2:18][C:19]([OH:21])=[O:20])[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:26])[CH:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59597898tert-butyl 2-(2-(4-methoxy-N,2,6-trimethylphenyl-sulfonamido)ethoxy)acetate

Product 1

HCID 46870354{2-[(4-methoxy-2,6-dimethyl-benzenesulfonyl)-methyl-amino]-ethoxy}acetic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 2-(2-(4-methoxy-N,2,6-trimethylphenylsulfonamido)ethoxy)acetate (124.5 g, 321.3 mmol) was dissolved in THF (1,150 ml) and MeOH (1,900 ml), and an aqueous 6 M NaOH solution (1,300 ml) was added. The reaction mixture was stirred at room temperature for 1 hour and the organic solvents were then distilled off. The residue was taken up in aqueous 6 M HCl (2,000 ml) at 0° C. and the mixture was extracted with methylene chloride (2×1,000 ml). The combined organic phases were dried, filtered and concentrated to dryness in vacuo. The yield was 103.5 g (97%).

Workup

  1. distillationthe organic solvents were then distilled off
  2. customwas taken up in aqueous 6 M HCl (2,000 ml) at 0° C.
  3. extractionthe mixture was extracted with methylene chloride (2×1,000 ml)
  4. customThe combined organic phases were dried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-536c1723b7c8450e947f53dab7775f29
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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