Sodium Hydroxide → (2S,4S)-1-(tert-Butoxycarbonyl)-4-phenoxy-2-pyrrolidinecarboxylic acid

HRID 1372587Notes

Reaction equation

HRID 1372587 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][C@H:9]1[C:20]([O:22]C)=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][C@H:9]1[C:20]([OH:22])=[O:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10710901HCID 10710901, compound

Product 1

HCID 2756009(2S,4S)-1-(tert-Butoxycarbonyl)-4-phenoxy-2-pyrrolidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylate (5.31 g, 16.5 mmol) in THF (132 ml) was added 0.25N NaOH (132 ml, 33.0 mmol). The reaction mixture was stirred overnight at room temperature. The residue obtained by concentrating the reaction mixture under reduced pressure was acidified with 1N HCl, followed by extraction with chloroform. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The crude crystals thus obtained were recrystallized from hexane-chloroform, whereby the title compound (2.96 g, 58%) was obtained as a white crystalline powder.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. extractionfollowed by extraction with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe crude crystals thus obtained
  9. customwere recrystallized from hexane-chloroform, whereby the title compound (2.96 g, 58%)
  10. customwas obtained as a white crystalline powder

Sources & evidence

ORD record
ord-3525d67e16484d689f5778dbb4377c40
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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