Potassium Carbonate → 2-(Hydroxymethyl)thiazole-4-carboxylic acid

HRID 520581Notes

Reaction equation

HRID 520581 reaction equation
CC(C)(C)C([O:5][CH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12]([OH:14])=[O:13])[N:11]=1)=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[OH:5][CH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12]([OH:14])=[O:13])[N:11]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 110968202-(2,2-Dimethyl-propionyloxymethyl)-thiazole-4-carboxylic acid

Product 1

HCID 235881312-(Hydroxymethyl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

A solution of 2-{[(2,2-dimethylpropanoyl)oxy]methyl}-1,3-thiazole-4-carboxylic acid (3 g) and potassium carbonate (2.326 g) in methanol (100 ml) and water (30 ml) was heated to reflux for 4 h. The mixture was cooled and concentrated in vacuo to −30 ml. It was then acidified with 2 M HCl (aq) (50 ml) and concentrated in vacuo. The resulting solid was treated with hot MeOH/Ethyl acetate (2:1), washing well before filtering off the remaining solid. The filtrate was concentrated in vacuo to give a brown solid which was dissolved in MeOH and added to the top of 2×70 g aminopropyl cartridge that had been preconditioned with MeOH. The cartridges were both eluted with MeOH and then with 10% HCl in MeOH. The acidic fractions were combined and the solvent removed in vacuo to give the title compound as a brown oil, 550 mg.

Workup

  1. temperatureto reflux for 4 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo to −30 ml
  4. concentrationconcentrated in vacuo
  5. additionThe resulting solid was treated with hot MeOH/Ethyl acetate (2:1)
  6. washwashing well
  7. filtrationbefore filtering off the remaining solid
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give a brown solid which
  10. additionadded to the top of 2×70 g aminopropyl cartridge that
  11. washboth eluted with MeOH
  12. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cfd959b8448744c7bf23b305c0885015
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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