Acetic Acid → HCID 22344625, compound

HRID 2299825Notes

Reaction equation

HRID 2299825 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:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([NH2:32])=[O:31].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:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)\[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([NH2:32])=[O:31])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 22344577HCID 22344577, compoundHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

Product 1

HCID 22344625HCID 22344625, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (600 mg), 6-oxo-6-phenylhexanamide (396 mg), acetic acid (0.331 ml), sodium acetate (317 mg) and ethanol (20 ml) was heated to reflux for 18 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 to obtain crystals from an ethyl acetate-hexane (3:1, v/v)-eluted fraction. The crystals were recrystallized from ethyl acetate-hexane to obtain E-6-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-6-phenylhexanamide (651 mg, yield 68%) as colorless crystals. m.p. 95-96° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 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. customto obtain crystals from an ethyl acetate-hexane (3:1, v/v)-eluted fraction
  8. customThe crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8ccf6ca93bac4b08aa667ccf64d61d44
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

Loading…