Acetic Acid → HCID 69434401, compound

HRID 1295279Notes

Reaction equation

HRID 1295279 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH:25]([C:32](=O)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=O)=[CH:17][CH:16]=1.C([O-])(=O)C.[NH4+:44].C(O)(=O)C>C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[O:24][C:25]([CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[C:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:44]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 69428068HCID 69428068, compound

Product 1

HCID 69434401HCID 69434401, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]acetoxy-5-oxo-5-phenylpentanoate (1.34 g), ammonium acetate (685 mg) and acetic acid (5 ml) was refluxed for 3 hrs. After cooling, ethyl acetate was added to the reaction mixture. The obtained ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate and then saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-[2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-phenyl-5-oxazolyl]propionate (1.07 g, yield 83%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:5, volume ratio).

Workup

  1. temperaturewas refluxed for 3 hrs
  2. temperatureAfter cooling
  3. washThe obtained ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialsaturated brine, dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-de769635a61a465e91a29c9d3623beab
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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