Hydrochloric Acid → 4-Thiazolecarboxylic acid, 2-propyl-, ethyl ester

HRID 1689340Notes

Reaction equation

HRID 1689340 reaction equation
Cl.[C:2]([NH:7][CH:8]([CH2:14][SH:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=O)[CH2:3][CH2:4][CH3:5]>C(O)C>[CH2:3]([C:2]1[S:15][CH:14]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1)[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57989348Ethyl 2-butyramido-3-mercaptopropanoate

Product 1

HCID 2036314-Thiazolecarboxylic acid, 2-propyl-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of HCl (4M in 1,4-dioxane, 20 mL) was added to a solution of ethyl 2-butyramido-3-mercaptopropanoate (example 56, step a) (3 g) in ethanol (20 mL) and the resulting mixture stirred overnight. The solvent was evaporated and the residue azeotroped twice with toluene. The residue was redissolved in acetonitrile (50 mL), manganese dioxide (11.9 g) was added and the mixture heated at reflux overnight. The reaction was filtered through a pad of Celite. The filter pad was washed with MeCN (3×100 mL). The combined filtrate and washings were evaporated and the residue was purified by silica gel chromatography eluting with 9:1 isohexane:ethyl acetate. The product containing fractions were combined and evaporated to give the subtitled compound as a clear oil. Yield 0.24 g.

Workup

  1. customThe solvent was evaporated
  2. customthe residue azeotroped twice with toluene
  3. dissolutionThe residue was redissolved in acetonitrile (50 mL)
  4. additionmanganese dioxide (11.9 g) was added
  5. temperaturethe mixture heated
  6. temperatureat reflux overnight
  7. filtrationThe reaction was filtered through a pad of Celite
  8. washThe filter pad was washed with MeCN (3×100 mL)
  9. customThe combined filtrate and washings were evaporated
  10. customthe residue was purified by silica gel chromatography
  11. washeluting with 9:1 isohexane
  12. additionThe product containing fractions
  13. customevaporated

Sources & evidence

ORD record
ord-150d7507685d4be09e2c6c14b52a606c
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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