Acetic Acid → HCID 9912511, compound

HRID 2299878Notes

Reaction equation

HRID 2299878 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:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1.O=[C:25]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:26][CH2:27][C:28]([NH2:30])=[O:29].C(O)(=O)C.C([O-])(=O)C.[Na+]>O.C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:25](\[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)/[CH2:26][CH2:27][C:28]([NH2:30])=[O:29])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 5200224-Oxo-4-phenylbutanamideHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

Product 1

HCID 9912511HCID 9912511, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (1.00 g), 4-oxo-4-phenylbutanamide (571 mg), acetic acid (0.553 ml), sodium acetate (528 mg) and ethanol (20 ml) was heated to reflux for 10 hours, the mixture was cooled to room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography and concentrated a portion from an ethyl acetate-hexane (3:1, v/v)-eluted fraction which eluted following the E-compound, to obtain crystals. The crystals were recrystallized from ethanol to obtain Z-4-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutanamide (120 mg, yield 8%) as colorless crystals. m.p. 110-112° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 10 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. concentrationconcentrated a portion from an ethyl acetate-hexane (3:1, v/v)-eluted fraction which
  8. washeluted
  9. customto obtain crystals
  10. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-8edaba6b8a1c43b491ea757110b86549
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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