Ammonium Acetate → HCID 178434979, compound

HRID 2219351Notes

Reaction equation

HRID 2219351 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([C:16]1[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:18][O:19][C:20]=1[CH3:21])=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:32]>C(O)(=O)C>[CH2:1]([O:8][CH2:9][C:10]1[NH:12][CH:13]=[C:14]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][O:19][C:20]=2[CH3:21])[N:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 67420627HCID 67420627, compound

Product 1

HCID 178434979HCID 178434979, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a refluxing solution of 2-benzyloxy-N-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-2-oxo-ethyl]-acetamide (3.35 g, 9 mmol) in acetic acid (10 mL) was added ammonium acetate (14.2 g, 184 mmol) portionwise over 1.5 h. Then the mixture was heated for a subsequent 2 h under reflux and then allowed to cool down to room temperature overnight. The mixture was then poured onto water and extracted with ethyl acetate. The organic layer was then washed with water and brine, dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (2.36 g, 74%) which was obtained as a light yellow solid. MS: m/e=346.1 [M+H]+.

Workup

  1. temperatureThen the mixture was heated for a subsequent 2 h
  2. temperatureunder reflux
  3. additionThe mixture was then poured onto water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was then washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

Sources & evidence

ORD record
ord-4f2a338f4e5b4629be9cc3f35a0c3df3
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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