Triethylamine → HCID 15870474, compound

HRID 1603837Notes

Reaction equation

HRID 1603837 reaction equation
N1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH2:17][CH:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][N:14]=3)=[CH:9][CH:8]=2)CC=CCC1.C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C.C([O:33][CH2:34][C:35](Cl)=[O:36])(=O)C.[C:38](=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[OH:33][CH2:34][C:35]([N:25]1[CH2:26][CH:27]=[C:38]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH2:17][CH:16]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[O:15][N:14]=3)=[CH:11][CH:12]=2)[CH2:29][CH2:28]1)=[O:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 26297Acetoxyacetyl chlorideHCID 70111126HCID 70111126, compound

Product 1

HCID 15870474HCID 15870474, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask containing N-[[4,5-dihydro-3-[4-[1,2,3,6-tetrahydropyridinyl]-phenyl]-5-isoxazolyl]methyl]acetamide (185 mg, 0.62 mmol) in methylene chloride (20 mL) and triethylamine (0.17 mL, 1.24 mmol) is added acetoxyacetyl chloride (0.09 mL, 0.81 mmol) at 0° C. under an inert atmosphere. The reaction is warmed to ambient temperature, stirred for 2 hours and concentrated in vacuo. The residue is dissolved in methanol (15 mL) and potassium carbonate (260 mg, 1.88 mmol) is added. The reaction is stirred fifteen hours, concentrated in vacuo, and chromatographed on silica gel (230-400 mesh, 100 mL), eluting with chloroform/methanol (98/2). The appropriate fractions are combined (Rf =0.10, TLC, chloroform/methanol, 95/5) and concentrated in vacuo to give the title compound, mp 115-118° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in methanol (15 mL)
  3. stirringThe reaction is stirred fifteen hours
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica gel (230-400 mesh, 100 mL)
  6. washeluting with chloroform/methanol (98/2)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a968064bf59f45ddaee4fd420d3e2957
Source dataset
uspto-grants-1999_11
Patent number
US05990136

Reaction notes

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