2-Acetylamino-5-(3-ethylphenyl)-3-oxo-pentanoic acid, ethyl ester → 5-[2-(3-Ethylphenyl)ethyl]-2-methyloxazole-4-carboxylic acid, ethyl ester

HRID 324460Notes

Reaction equation

HRID 324460 reaction equation
[C:1]([NH:4][CH:5]([C:11](=[O:22])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH3:21])[CH:15]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH3:2]>S(Cl)(Cl)=O>[CH2:20]([C:16]1[CH:15]=[C:14]([CH2:13][CH2:12][C:11]2[O:22][C:1]([CH3:2])=[N:4][C:5]=2[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:19]=[CH:18][CH:17]=1)[CH3:21]

Participants

3

Reactant 1

HCID 1317225242-Acetylamino-5-(3-ethylphenyl)-3-oxo-pentanoic acid, ethyl ester

Product 1

HCID 1317225255-[2-(3-Ethylphenyl)ethyl]-2-methyloxazole-4-carboxylic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Thionyl chloride (80 ml) was added to the product from step (v) (21.0 g) at 0° C. The mixture was stirred at room temperature for 1 hour and heated at reflux for 1 hour. The residue after evaporation was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried (MgSO4) and evaporated.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customThe residue after evaporation
  4. dissolutionwas dissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate solution
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-8717d8d2bbf64cc0a2600a76080297a3
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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