Sodium Hydroxide → 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]propionic acid

HRID 1720592Notes

Reaction equation

HRID 1720592 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:13]([CH3:18])[C:14]([O:16]C)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:13]([CH3:18])[C:14]([OH:16])=[O:15])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54285520methyl 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]propionate

Product 1

HCID 105217632(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]propionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]propionate (1.05 g, 2.89 mmol) in tetrahydrofuran (60 mL) at room temperature is added 1N aqueous sodium hydroxide (8.6 mL, 8.67 mmol). The reaction mixture is stirred for 19 hours at room temperature. The tetrahydrofuran is then evaporated. The remaining residue is acidified with 1N hydrochloric acid and extracted with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated to give 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]propionic acid.

Workup

  1. customThe tetrahydrofuran is then evaporated
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-f3d7ab3849694152a08135f7f837bb2d
Source dataset
uspto-grants-1996_04
Patent number
US05506242

Reaction notes

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