Sodium Hydroxide → 2-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acid

HRID 1924003Notes

Reaction equation

HRID 1924003 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[CH2:21][O:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])(=[O:14])=[O:13])=[C:7]([CH3:31])[CH:6]=1>C1COCC1.CO>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([S:12]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]2[CH2:21][O:22][CH2:23][C:24]([OH:26])=[O:25])(=[O:14])=[O:13])=[C:7]([CH3:31])[CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57916265tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetate

Product 1

HCID 574368002-((1-(4-Methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaOH (6 M, 200 ml, 1200 mmole) was added to a solution of tert.-butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)methoxy)acetate (26.8 g, 62.7 mmole) in THF (200 ml) and methanol (200 ml). The reaction mixture was stirred at RT. After 1 hour the organic solvent was distilled off on a rotary evaporator and HCl (6 M, 210 ml) was added at 0° C. The aqueous phase was extracted with DCM (200 ml) and ethyl acetate (200 ml). The combined organic phases were dried over sodium sulfate and concentrated. Diisopropyl ether was added twice and evaporated. Yield: 21.92 g, 94%.

Workup

  1. distillationAfter 1 hour the organic solvent was distilled off on a rotary evaporator and HCl (6 M, 210 ml)
  2. additionwas added at 0° C
  3. extractionThe aqueous phase was extracted with DCM (200 ml) and ethyl acetate (200 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated
  6. additionDiisopropyl ether was added twice
  7. customevaporated

Sources & evidence

ORD record
ord-4ee4efc69d11404b9bb31f816ec95e1b
Source dataset
uspto-grants-2012_05
Patent number
US08178535B2

Reaction notes

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