Sodium Hydroxide → HCID 68962851, compound

HRID 2376121Notes

Reaction equation

HRID 2376121 reaction equation
C([O:3][C:4](=[O:26])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[CH:9][C:10]([NH:13][C@@H: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)=[N:11][CH:12]=1)C.[OH-].[Na+]>CO.C1COCC1>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][C@@H:14]([NH:13][C:10]2[N:11]=[CH:12][C:7](/[CH:6]=[CH:5]/[C:4]([OH:26])=[O:3])=[CH:8][CH:9]=2)[CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86603731HCID 86603731, compound

Product 1

HCID 68962851HCID 68962851, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of tert-butyl (3R)-3-({5-[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]-2-pyridinyl}amino)-1-pyrrolidinecarboxylate (600 mg) and 1N NaOH solution (3.3 ml) in MeOH (10 ml) and THF (10 ml) was stirred at 70-75° C. for 2 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of AcOEt and H2O. The aqueous solution was adjusted to PH4.5 and extracted with AcOEt and THF. The organic layer was washed with brine and dried over MgSO4. The solvent was concentrated in vacuo and the precipitate was collected by filtration to give (2E)-3-(6-{[(3R)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylic acid (0.45 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of AcOEt and H2O
  3. extractionextracted with AcOEt and THF
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationThe solvent was concentrated in vacuo
  7. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-00f900db168b4f9f8d27f42dfd8390bb
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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