Sodium Hydroxide → 3-Methylsulfanyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid

HRID 852664Notes

Reaction equation

HRID 852664 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([S:10][CH3:11])[CH:7]=[C:6]([NH:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16]Cl)[CH:5]=1.[OH-].[Na+]>CO>[CH3:11][S:10][C:8]1[CH:9]=[C:4]([CH:5]=[C:6]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:18])[CH:7]=1)[C:3]([OH:2])=[O:19]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 693577003-(4-Chloro-butanoylamino)-5-methylsulfanyl-benzoic acid methyl ester

Product 1

HCID 693576453-Methylsulfanyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-methylsulfanyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B1) (115 mg, 0.433 mmol, 1 equiv) in MeOH (8 ml) was added 2N aqueous NaOH solution (0.65 ml, 1.3 mmol, 3 equiv). The resulting mixture was stirred for 4 h, 2N aqueous NaOH solution (1 ml, mmol, equiv) was added and the resulting solution was stirred for 16 h then concentrated in vacuo. The residue was diluted with H2O and extracted with Et2O. The aqueous layer was acidified using 2N aqueous HCl solution and the white precipitate formed was extracted twice with AcOEt. The combined organic solutions were dried over Na2SO4 and concentrated in vacuo to give 3-methylsulfanyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (A1) (109 mg, 100%) as a white solid. [M+H]+=252.0, RT=2.61 min

Workup

  1. stirringthe resulting solution was stirred for 16 h
  2. concentrationthen concentrated in vacuo
  3. additionThe residue was diluted with H2O
  4. extractionextracted with Et2O
  5. customthe white precipitate formed
  6. extractionwas extracted twice with AcOEt
  7. dry with materialThe combined organic solutions were dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1f5ac84726c4e7f9f982d71128b0c0f
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…