Hydrochloric Acid → 2-Cyclopentylthiazole-4-carboxylic acid

HRID 1689354Notes

Reaction equation

HRID 1689354 reaction equation
O.[OH-].[Li+].[CH:4]1([C:9]2[S:10][CH:11]=[C:12]([C:14]([O:16]CC)=[O:15])[N:13]=2)[CH2:8][CH2:7][CH2:6][CH2:5]1.Cl>C1COCC1.O>[CH:4]1([C:9]2[S:10][CH:11]=[C:12]([C:14]([OH:16])=[O:15])[N:13]=2)[CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57989290Ethyl 2-cyclopentylthiazole-4-carboxylate

Product 1

HCID 579891322-Cyclopentylthiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (0.67 g) was added to solution of ethyl 2-cyclopentylthiazole-4-carboxylate (example 59, step c) (0.9 g) in a mixture of THF (40 mL) and water (10 mL). The resulting mixture was stirred overnight. The reaction was acidified with aqueous HCl solution (2M, 10 mL) and the solvent evaporated. The residue was partitioned between brine (50 mL) and ethyl acetate (50 mL) and the layers separated. The aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic solutions were dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a pale yellow solid. Yield 0.77 g.

Workup

  1. customthe solvent evaporated
  2. customThe residue was partitioned between brine (50 mL) and ethyl acetate (50 mL)
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic solutions were dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d8e5ead9430147ff9d0eccb01538201a
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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