Acetic Acid → HCID 57855715, compound

HRID 475588Notes

Reaction equation

HRID 475588 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:14][CH:15]=[C:16]([CH2:18][CH:19]([C:24]([C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=3)=[O:25])C(OC)=O)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].C(O)(=O)C.Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:14][CH:15]=[C:16]([CH2:18][CH2:19][C:24]([C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=3)=[O:25])[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68982394HCID 68982394, compound

Product 1

HCID 57855715HCID 57855715, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A 0.8 g quantity or methyl 2-[2-(3,4-diethoxyphenyl)oxazol-4-ylmethyl]-3-(3-methylpyridin-2-yl)-3-oxopropionate obtained in Example 180 was added to a mixture of 5 ml acetic acid and 1.5 ml of concentrated hydrochloric acid, and the resulting mixture was stirred at 110° C. for 4 hours. After cooling the obtained solution to room temperature, 30 ml of ethyl acetate and 30 ml of saturated sodium hydrogen carbonate solution were gradually added thereto with stirring, and stirring was further continued. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=3:1), and further recrystallized from ethyl acetate/n-hexane to give 0.28 g of white powdery 3-[2-(3,4-diethoxyphenyl)oxazol-4-yl]-1-(3-methylpyridin-2-yl)propan-1-one.

Workup

  1. temperatureAfter cooling the obtained solution to room temperature
  2. stirringwith stirring
  3. stirringstirring
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=3:1)
  7. customfurther recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-568871e6e4234db680756e28f8f59b05
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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