Sodium Hydroxide → 3-Benzyloxy-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yloxy)butyric acid

HRID 1941107Notes

Reaction equation

HRID 1941107 reaction equation
[CH2:1]([O:8][C:9]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:26])[CH:10]([O:15][C:16]1[N:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[N:17]=1)[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O1CCCC1>[CH2:1]([O:8][C:9]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:26])[CH:10]([O:15][C:16]1[N:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[N:17]=1)[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15292273Methyl 3-benzyloxy-3-phenyl-2-(4,6-dimethoxy-2-pyrimidinyl)oxybutyrate

Product 1

HCID 152922743-Benzyloxy-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yloxy)butyric acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.4 g (3 mmol) of methyl 3-benzyloxy-3-phenyl-2-(4,6-dimethoxypyrimidin-2-yloxy)butyrate (Example 3) are dissolved in 20 ml of methanol and 20 ml of tetrahydrofuran, and 3.7 g of 10% strength NaOH solution are added. Stirring is carried out for 6 hours at 60° C. and for 12 hours at room temperature, the solvent is distilled off under reduced pressure and the residue is taken up in 100 ml of water. Extraction is now carried out with ethyl acetate to remove unconverted ester. The aqueous phase is then brought to pH 1-2 with dilute hydrochloric acid and is extracted with ethyl acetate. After drying has been carried out over magnesium sulfate and the solvent has been distilled off, a little acetone is added to the residue and the precipitate formed is filtered off with suction. After drying, 1.2 g of a white powder remain.

Workup

  1. distillationthe solvent is distilled off under reduced pressure
  2. extractionExtraction
  3. customto remove unconverted ester
  4. extractionis extracted with ethyl acetate
  5. customAfter drying
  6. distillationthe solvent has been distilled off
  7. additiona little acetone is added to the residue
  8. customthe precipitate formed
  9. filtrationis filtered off with suction
  10. customAfter drying

Sources & evidence

ORD record
ord-b0d2a2dbee6a4635a67e22d7b2b952d0
Source dataset
uspto-grants-1997_12
Patent number
US05703017

Reaction notes

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