Lithium Hydroxide → 4-(1-Tert-butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid

HRID 412550Notes

Reaction equation

HRID 412550 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]2)=[CH:9][CH:8]=1)C.[OH-].[Li+]>O1CCCC1.C(O)C>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:14]([O:13][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:26])=[O:3])=[CH:12][CH:11]=2)[CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 600642154-(1-tert-Butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid ethyl ester

Product 1

HCID 185363434-(1-Tert-butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acidYield 99.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid ethyl ester (2.5 g) in a mixture of tetrahydrofuran (5 ml) and ethanol (5 ml) was added 1N aqueous lithium hydroxide solution (7.5 ml) with ice-cooling, and the mixture was stirred at room temperature for 30 min. After completion of the reaction, the solvent was evaporated and to the obtained residue were added ice water and 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was dried under reduced pressure to give the title compound(2.30 g).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated and to the obtained residue
  4. additionwere added ice water and 10% aqueous citric acid solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed successively with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-b66f0f746141458c9a594ff45484dda6
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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