Sodium Hydroxide → 3-(1-(4-chloro-2,5-dimethylphenylsulfonyl)piperidin-2-yl)propionic Acid

HRID 1924004Notes

Reaction equation

HRID 1924004 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][CH2:21][C:22]([O:24]C)=[O:23])(=[O:13])=[O:12])=[C:6]([CH3:26])[CH:5]=1>C1COCC1>[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([S:11]([N:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]2[CH2:20][CH2:21][C:22]([OH:24])=[O:23])(=[O:12])=[O:13])=[C:6]([CH3:26])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59820132Methyl 3-(1-(4-chloro-2,5-dimethylphenylsulfonyl)piperidin-2-yl)propionate

Product 1

HCID 574367993-(1-(4-chloro-2,5-dimethylphenylsulfonyl)piperidin-2-yl)propionic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Aqueous NaOH solution (6 M, 100 ml) was added to a solution of methyl 3-(1-(4-chloro-2,5-dimethylphenylsulfonyl)piperidin-2-yl)propionate (12.82 g, 34.3 mmole) in THF (100 ml). After 1 hour's reaction time the solvent was removed on a rotary evaporator and the solution was cooled to 0° C. HCl (6 M, 100 ml) was added and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. Yield: 12.36 g, 100%.

Workup

  1. customAfter 1 hour's reaction time the solvent
  2. customwas removed on a rotary evaporator
  3. additionHCl (6 M, 100 ml) was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e174086a84364068b49ddf03d2bf253a
Source dataset
uspto-grants-2012_05
Patent number
US08178535B2

Reaction notes

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