Sodium Hydroxide → HCID 68960937, compound

HRID 226311Notes

Reaction equation

HRID 226311 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[N:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([O:25]CC)=[O:24])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:9][CH2:10][CH:11]([NH:14][C:15]3[N:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)=[O:7])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86603615HCID 86603615, compound

Product 1

HCID 68960937HCID 68960937, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of ethyl (2E)-3-(6-{[1-(4-chlorobenzoyl)-4-piperidyl]amino}-3-pyridyl)acrylate (190 mg) and 1N NaOH solution (1.0 ml) in MeOH (20 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 water. The aqueous solution was adjusted to PH4.5 and extract 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-{[1-(4-chlorobenzoyl)-4-piperidyl]amino}-3-pyridyl)acrylic acid (85 mg)

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of AcOEt and water
  3. extractionextract 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-0f13d661ff694150a7671bd9c701f139
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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