Lithium Hydroxide → 2-(Propan-2-yl)-1,3-thiazole-5-carboxylic acid

HRID 471107Notes

Reaction equation

HRID 471107 reaction equation
[CH:1]([C:4]1[S:5][C:6]([C:9]([O:11]CC)=[O:10])=[CH:7][N:8]=1)([CH3:3])[CH3:2].[OH-].[Li+]>CO.O>[CH:1]([C:4]1[S:5][C:6]([C:9]([OH:11])=[O:10])=[CH:7][N:8]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10608068Ethyl 2-isopropylthiazole-5-carboxylate

Product 1

HCID 197863422-(Propan-2-yl)-1,3-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 2-isopropylthiazole-5-carboxylate (example 55, step a) (0.33 g) in methanol (6 mL) was treated with a solution of lithium hydroxide (0.079 g) in water (3 mL) and the resultant mixture stirred for 2 hours at 20° C. The methanol was evaporated off under reduced pressure and the residue partitioned between ether and brine. The aqueous layer was acidified by dropwise addition of dilute hydrochloric acid and the mixture extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.185 g.

Workup

  1. customThe methanol was evaporated off under reduced pressure
  2. customthe residue partitioned between ether and brine
  3. additionThe aqueous layer was acidified by dropwise addition of dilute hydrochloric acid
  4. extractionthe mixture extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-963a51a475b74d05b0e73652652ef381
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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