Hydrochloric Acid → 2-Cyclopentylthiazole-4-carboxylic acid

HRID 1255289Notes

Reaction equation

HRID 1255289 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 [Carboxylic Acid 2, 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 (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 titled 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-4c7e1777ed75463aa4f4896238a53833
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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