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

HRID 2388654Notes

Reaction equation

HRID 2388654 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.C(OC(C)C)(C)C>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

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 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

A 6 M aqueous NaOH solution (200 ml, 1.200 mmol) 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 mmol) in THF (200 ml) and methanol (200 ml) and the reaction was stirred at room temperature for 1 hour. The organic solvents were then distilled off and 6 M aqueous HCl (210 ml) was added to the residue at 0° C. The aqueous phase was extracted with methylene chloride (200 ml) and ethyl acetate (200 ml). The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. The residue obtained was codistilled twice with diisopropyl ether. The yield was 21.92 g (94%).

Workup

  1. distillationThe organic solvents were then distilled off
  2. addition6 M aqueous HCl (210 ml) was added to the residue at 0° C
  3. extractionThe aqueous phase was extracted with methylene chloride (200 ml) and ethyl acetate (200 ml)
  4. dry with materialThe combined organic phases were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained

Sources & evidence

ORD record
ord-c1c6e849327449059e3eb68c2d468c24
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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