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

HRID 45988Notes

Reaction equation

HRID 45988 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 1-[(4-chloro-2,5-dimethylphenyl)sulfonyl]-2-piperidinepropanoate

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 mmol) in THF (100 ml). After a reaction time of 1 h, the solvent was removed on a rotary evaporator and the residue 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 Na2SO4 and concentrated. Yield: 12.36 g, 100%.

Workup

  1. customAfter a reaction time of 1 h, the solvent was removed on a rotary evaporator
  2. additionHCl (6 M, 100 ml) was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-702df0c516534255a94198dc705abb0d
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Reaction notes

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