Water → 3,5-bis(2-oxopyrrolidin-1-yl)benzoic Acid

HRID 1612434Notes

Reaction equation

HRID 1612434 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([N:16]2[CH2:20][CH2:19][CH2:18][C:17]2=[O:21])[CH:5]=1.[Li+].[OH-].O>O1CCOCC1>[O:21]=[C:17]1[CH2:18][CH2:19][CH2:20][N:16]1[C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=1)[C:3]([OH:22])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 693577583,5-Bis-(2-oxo-pyrrolidin-1-yl)benzoic Acid Methyl Ester

Product 1

HCID 111620233,5-bis(2-oxopyrrolidin-1-yl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3,5-bis-(2-oxopyrrolidin-1-yl)benzoic acid methyl ester (D7) (201 mg, 0.666 mmol) in dioxane (2 ml) was treated with LiOH (42 mg, 0.998 mmol) and water (1 ml). The reaction mixture was stirred for 2 hours at room temperature. The solvent was then evaporated to dryness and the residue was partitioned between ethyl acetate and water. The aqueous layer was separated and acidified to pH=1. The product precipitated in the aqueous layer and was removed by filtration and dried in vacuo to D8 (128 mg) as white solid.

Workup

  1. customThe solvent was then evaporated to dryness
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe aqueous layer was separated
  4. customThe product precipitated in the aqueous layer
  5. customwas removed by filtration
  6. dry with materialdried in vacuo to D8 (128 mg) as white solid

Sources & evidence

ORD record
ord-4d51accdffa34bd39ad3b01d8a301aaf
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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