Methanol → 3-[Methyl(methylsulfonyl)amino]-5-(2-oxo-4-phenylpyrrolidin-1-yl)benzoic acid

HRID 1160455Notes

Reaction equation

HRID 1160455 reaction equation
[CH3:1][N:2]([S:25]([CH3:28])(=[O:27])=[O:26])[C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH2:17][CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][C:14]2=[O:24])[CH:12]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+].CO>O1CCCC1>[CH3:1][N:2]([S:25]([CH3:28])(=[O:27])=[O:26])[C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH2:17][CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][C:14]2=[O:24])[CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57815124Methyl 3-[methyl(methylsulfonyl)amino]-5-(2-oxo-4-phenylpyrrolidin-1-yl)benzoate

Product 1

HCID 578150783-[Methyl(methylsulfonyl)amino]-5-(2-oxo-4-phenylpyrrolidin-1-yl)benzoic acidYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-[methyl(methylsulfonyl)amino]-5-(2-oxo-4-phenylpyrrolidin-1-yl)benzoate obtained in Reference Example 18 329 mg (0.32 mmol), 2N aqueous sodium hydroxide solution (0.5 mL), methanol (0.5 mL) and tetrahydrofuran (0.5 mL) was stirred at room temperature for 15 hours. The solvent was concentrated and the mixture was adjusted by adding 1N hydrochloric acid to pH=3 and the mixture was extracted with ethyl acetate. After drying of the mixture on magnesium sulfate, the solvent was evaporated to give 113 mg (0.291 mmol) of the title compound (yield: 91%).

Workup

  1. concentrationThe solvent was concentrated
  2. additionby adding 1N hydrochloric acid to pH=3
  3. extractionthe mixture was extracted with ethyl acetate
  4. customAfter drying of the mixture on magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-69012cf08795437fbf7b85ad4e78b77e
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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