Acetic Acid → HCID 178470934, compound

HRID 1496977Notes

Reaction equation

HRID 1496977 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([C:15]([C:17]2[S:18][C:19]([CH3:22])=[CH:20][N:21]=2)=O)[CH:12]=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:23]([OH:26])(=[O:25])[CH3:24].O.[CH2:28](O)[CH3:29]>C1COCC1.[Pd]>[OH:8][C:9]1[N:14]=[C:13]([CH:15]([C:17]2[S:18][C:19]([CH3:22])=[CH:20][N:21]=2)[CH2:24][C:23]([O:26][CH2:28][CH3:29])=[O:25])[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 962WaterHCID 117600382HCID 117600382, compound

Product 1

HCID 178470934HCID 178470934, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (6-(benzyloxy)pyridin-2-yl)(5-methylthiazol-2-yl)methanone (8.0 g, 21 mmol), acetic acid (1.5 mL), H2O (3 mL), and Pd/C (10%, 4 g) in ethanol (90 mL) and THF (60 mL) was stirred under H2 atmosphere at room temperature overnight. After filtration through a pad of Celite and evaporation of the solvent, the residue was washed with MTBE and petroleum ether to afford A030-7 (3 g) as a white solid. The filtration (mixture of A030-6 and A030-7) was mixed with TFA (20 mL) and the resulting mixture was refluxed for 2 h. After cooling down, the mixture was treated with water and extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was washed with MTBE and petroleum ether to afford ethyl 3-(6-hydroxypyridin-2-yl)-3-(5-methylthiazol-2-yl)propanoate (1.4 g, total 71%) as a white solid.

Workup

  1. filtrationAfter filtration
  2. customthrough a pad of Celite and evaporation of the solvent
  3. washthe residue was washed with MTBE and petroleum ether
  4. customto afford A030-7 (3 g) as a white solid
  5. filtrationThe filtration (
  6. additionmixture of A030-6
  7. additionA030-7) was mixed with TFA (20 mL)
  8. temperaturethe resulting mixture was refluxed for 2 h
  9. temperatureAfter cooling down
  10. additionthe mixture was treated with water
  11. extractionextracted with ethyl acetate
  12. customThe organic layer was dried
  13. concentrationconcentrated
  14. washThe residue was washed with MTBE and petroleum ether

Sources & evidence

ORD record
ord-0131ba4d325e4e349163af25a0ac475c
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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