Hydrochloric Acid → 2-(2-Methylpropyl)-1,3-thiazole-4-carboxylic acid

HRID 1689384Notes

Reaction equation

HRID 1689384 reaction equation
O.[OH-].[Li+].[CH2:4]([C:8]1[S:9][CH:10]=[C:11]([C:13]([O:15]CC)=[O:14])[N:12]=1)[CH:5]([CH3:7])[CH3:6].Cl>C1COCC1.O>[CH2:4]([C:8]1[S:9][CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N:12]=1)[CH:5]([CH3:7])[CH3:6]

Participants

6

Procedure

Lithium hydroxide monohydrate (4.1 g) was added to a solution of ethyl 2-isobutylthiazole-4-carboxylate (example 72, step c) (5.2 g) in a mixture of THF (80 mL) and water (20 mL). The resulting mixture was stirred overnight. The reaction was carefully acidified with concentrated hydrochloric acid (10 mL) and the volatiles evaporated. The resulting aqueous mixture was poured into brine (50 mL) and extracted with ethyl acetate (3×100 mL). The combined organic solutions were washed with brine (50 mL), dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a white solid. Yield 3.8 g.

Workup

  1. customthe volatiles evaporated
  2. additionThe resulting aqueous mixture was poured into brine (50 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic solutions were washed with brine (50 mL)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-921d72a988e04052925bbeb0ec941317
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…