Lithium Hydroxide → 2-Fluoro-3-(2-oxopyrrolidin-1-yl)-5-trifluoromethyl Benzoic Acid

HRID 1612444Notes

Reaction equation

HRID 1612444 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])[C:5]=1[F:20].[Li+].[OH-]>O1CCOCC1>[F:20][C:5]1[C:6]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])=[CH:7][C:8]([C:10]([F:13])([F:11])[F:12])=[CH:9][C:4]=1[C:3]([OH:21])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 695896852-Fluoro-3-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic Acid Methyl Ester

Product 1

HCID 222530252-Fluoro-3-(2-oxopyrrolidin-1-yl)-5-trifluoromethyl Benzoic Acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Fluoro-3-(2-oxopyrrolidin-1-yl)-5-trifluoromethylbenzoic acid methyl ester (D24) in dioxane (10 ml) was treated with 1M LiOH solution (1.75 ml) and stirred at room temperature for 2 h. The dioxane was then removed under vacuum and dil. NaHCO3 and ethyl acetate were added. The aqueous phase was separated, washed with ethyl acetate, acidified with 1M HCl and extracted with ethyl acetate. The organic extract was washed with brine, dried over MgSO4 and evaporated to dryness to afford the title compound

Workup

  1. customThe dioxane was then removed under vacuum and dil. NaHCO3 and ethyl acetate
  2. additionwere added
  3. customThe aqueous phase was separated
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with brine
  8. dry with materialdried over MgSO4
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-87dd4952d83e465f8382db3c1073ad8f
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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