HCID 69331990, compound → HCID 69333253, compound

HRID 915010Notes

Reaction equation

HRID 915010 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:12]([CH:23]([CH3:29])[C:24]([O:26]CC)=[O:25])[C:13](=[O:22])[O:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5]1)([CH3:3])[CH3:2]>[OH-].[Na+].C1COCC1>[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11]2[N:12]([CH:23]([CH3:29])[C:24]([OH:26])=[O:25])[C:13](=[O:22])[O:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 69331990HCID 69331990, compound

Product 1

HCID 69333253HCID 69333253, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
52.5 °C

Procedure

A solution of ethyl 2-[4-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-5-phenyl-oxazol-3(2H)-yl]-propanoate (3.32 g) in a mixture of 1N aq. NaOH (25 ml) and THF (25 ml) was heated at 50-55° C. for 2 hours. After removal of THF, the mixture was acidified with 1N aq. HCl, extracted with EtOAc, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was recrystallized from a mixture of CHCl3 and n-hexane to give 2-[4-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-5-phenyl-oxazol-3(2H)-yl]propanoic acid as a solid (2.53 g).

Workup

  1. customAfter removal of THF
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue
  6. customThe residue was recrystallized from a mixture of CHCl3 and n-hexane

Sources & evidence

ORD record
ord-45ade042157b4e90945c2cf5721b55db
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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