Hydrochloric Acid → HCID 10875224, compound

HRID 584463Notes

Reaction equation

HRID 584463 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:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]C)=[O:34].Cl.C([O-])(=O)C.[Na+].[OH-].[Na+]>O1CCCC1.CO.O>[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:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:22][CH:23]=1

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 11054485HCID 11054485, compoundHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

Product 1

HCID 10875224HCID 10875224, compoundYield 37.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (500 mg), methyl 9-oxo-9-phenylnonanoate (464 mg), 1N hydrochloric acid (3 ml), sodium acetate (264 mg) and methanol (20 ml) was heated to reflux for 72 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 an oil from an ethyl acetate-hexane (1:6, v/v)-eluted fraction. This was dissolved in tetrahydrofuran (10 ml)-methanol (5 ml), a 1N aqueous saturated solution of sodium hydroxide (5 ml) was added and stirred at room temperature for 1 hour. 1N hydrochloric acid (5.5 ml) 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 recrystallized from ethyl acetate-hexane to obtain E-9-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-9-phenylnonanoic acid (323 mg, yield 37%) as colorless crystals. m.p. 67-68° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 72 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 an oil from an ethyl acetate-hexane (1:6, v/v)-eluted fraction
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-6d52a657b34743afab53f6e4b7229301
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

Loading…