Sodium Hydroxide → HCID 58431987, compound

HRID 56526Notes

Reaction equation

HRID 56526 reaction equation
[O:1]=[S:2]1(=[O:20])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:18][CH3:19])[C:14]([O:16]C)=[O:15])=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[O:1]=[S:2]1(=[O:20])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[CH:9][C:10]([CH:13]([O:18][CH3:19])[C:14]([OH:16])=[O:15])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58432115HCID 58432115, compound

Product 1

HCID 58431987HCID 58431987, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)-2-methoxyacetate (0.48 g, 1.6 mmol) in MeOH (21 mL) was added 1 M NaOH (7 mL, 7 mmol) slowly. After stirring at room temperature for 23 hrs, the volatiles were removed in vacuo and the residue was dissolved in H2O. EtOAc was added to the aqueous solution and saturated aqueous NH4Cl and 1 M HCl were added slowly until the pH ˜3. The mixture was extracted with EtOAc then the aqueous layer was acidified to pH 1 and extracted with EtOAc again. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo to give 2-(4-(1,1-dioxidoisothiazolidin-2-yl)phenyl)-2-methoxyacetic acid as a yellow foam (0.378 g, 82% yield). The product was used in the next synthetic step without further purification.

Workup

  1. customthe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in H2O
  3. additionEtOAc was added to the aqueous solution and saturated aqueous NH4Cl and 1 M HCl
  4. additionwere added slowly until the pH ˜3
  5. extractionThe mixture was extracted with EtOAc
  6. extractionextracted with EtOAc again
  7. washThe combined organics were washed with H2O and brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1d76b5fdf9844a3aeb42dab4622e324
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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