Sodium Hydroxide → HCID 69359156, compound

HRID 852667Notes

Reaction equation

HRID 852667 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[C:6]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[CH:5]=1.[OH-].[Na+]>C1COCC1>[O:20]=[C:16]1[CH2:17][CH2:18][CH2:19][N:15]1[C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([N:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[CH:7]=1)[C:3]([OH:21])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69359976HCID 69359976, compound

Product 1

HCID 69359156HCID 69359156, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 3-(2-oxo-pyrrolidin-1-yl)-5-pyrrolidin-1-yl-benzoic acid methyl ester (B113) (85 mg, 0.29 mmol, 11 equiv) in THF (5 ml) was added 1N aqueous NaOH solution (0.60 ml, 0.6 mmol, 2 equiv). The resulting mixture was stirred for 14 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 MgSO4 and concentrated in vacuo to give 3-(2-oxo-pyrrolidin-1-yl)-5-pyrrolidin-1-yl-benzoic acid (A113) (77 mg, 95%) as a white solid. [M+H]+=275.0, RT=2.72 min

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was diluted with H2O
  3. extractionextracted with Et2O
  4. customthe white precipitate formed
  5. extractionwas extracted twice with AcOEt
  6. dry with materialThe combined organic solutions were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0ae9ab95bdd3486fa31fd57049b63ec8
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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