Acetic Acid → HCID 22344558, compound

HRID 1070180Notes

Reaction equation

HRID 1070180 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.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=O)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[CH:27][CH:26]=1.[C:42](O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.CO>[Cl:24][C:25]1[CH:30]=[CH:29][C:28](/[C:31](=[N:21]/[O:20][CH2:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:6][C:2]=3[CH3:1])=[CH:23][CH:22]=2)/[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:42])=[O:39])=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamineHCID 223446108-(4-Chlorophenyl)-8-oxooctanoic acid

Product 1

HCID 22344558HCID 22344558, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (600 mg), 8-(4-chlorophenyl)-8-oxooctanoic acid (546 mg), acetic acid (0.331 ml), sodium acetate (317 mg) and methanol (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 methyl E-8-(4-chlorophenyl)-8-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino)octanoate (828 mg, yield 75%) as a colorless oil from an ethyl acetate-hexane (1:6, v/v)-eluted fraction.

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

Sources & evidence

ORD record
ord-2c027328e8e445f79d3903dc41004a1f
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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