Trifluoroacetic acid → HCID 57855723, compound

HRID 475597Notes

Reaction equation

HRID 475597 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([C:24]2[O:25][CH:26]=[C:27]([CH2:29][CH2:30][C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39]COC)=[O:32])[N:28]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:8]([O:15][C:16]1[CH:17]=[C:18]([C:24]2[O:25][CH:26]=[C:27]([CH2:29][CH2:30][C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[OH:39])=[O:32])[N:28]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57855866HCID 57855866, compound

Product 1

HCID 57855723HCID 57855723, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 60 ml quantity of trifluoroacetic acid was stirred with ice cooling, 12.3 g of the compound obtained in Example 231 was added thereto, and stirring was conducted for one hour. At the completion of the reaction, the reaction mixture was neutralized by addition of an aqueous saturated sodium bicarbonate solution, and ethyl acetate was added to the obtained mixture. The organic layer was washed twice with water, separated, concentrated under reduced pressure, and the obtained crude crystals were recrystallized from ethanol, thereby yielding 5.9 g of white powdery 3-[2-(3-benzyloxy-4-methoxyphenyl)oxazol-4-yl]-1-(2-hydroxyphenyl)propan-1-one.

Workup

  1. additionwas added
  2. customAt the completion of the reaction
  3. additionwas added to the obtained mixture
  4. washThe organic layer was washed twice with water
  5. customseparated
  6. concentrationconcentrated under reduced pressure
  7. customthe obtained crude crystals
  8. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-06c25f20950d4888b440264f4c1316fe
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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