Water → 5-(2-Oxopyrrolidin-1-yl)-biphenyl-3-carboxylic Acid

HRID 1612437Notes

Reaction equation

HRID 1612437 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:10]=1)=[O:4].[Li+].[OH-].O>O1CCOCC1>[O:16]=[C:12]1[CH2:13][CH2:14][CH2:15][N:11]1[C:9]1[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 695897705-(2-Oxopyrrolidin-1-yl)-biphenyl-3-carboxylic Acid Methyl Ester

Product 1

HCID 222529945-(2-Oxopyrrolidin-1-yl)-biphenyl-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 5-(2-oxopyrrolidin-1-yl)-biphenyl-3-carboxylic acid methyl ester (D10) (23 mg, 0.078 mmol) in dioxane (2 ml) was added LiOH (5 mg, 0.117 mmol) and water (1 ml) and stirred at room temperature for 2 hours. 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 afford D11 (10 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. customdried in vacuo
  7. customto afford D11 (10 mg) as white solid

Sources & evidence

ORD record
ord-d90817cd960e4005afaad5d26f2c7547
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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