Tetrabutylammonium Fluoride → HCID 89444237, compound

HRID 526004Notes

Reaction equation

HRID 526004 reaction equation
[C:1]([O:4]/[N:5]=[C:6](/[C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:12][CH:13]=1)\[NH2:7])(=O)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:2][C:1]1[O:4][N:5]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[N:12][CH:13]=2)[N:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89444616HCID 89444616, compound

Product 1

HCID 89444237HCID 89444237, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-[[5-[(Z)—N′-acetoxycarbamimidoyl]-2-pyridyl]amino]-4-oxo-butanoate (obtained in step 2, 0.18 g, 0.58 mmol, 1 equiv.) in tetrahydrofuran (20 mL) was added tetrabutylammonium fluoride (1.0 mol/L) in THF (0.053 g, 0.058 mL, 0.058 mmol, 0.1 equiv.) at room temperature. The mixture was stirred for 4 h at room temperature. The residue was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (3×50 ml). The combined organic layer was dried on magnesium sulfate, and then concentrated under vacuum. The residue was purified by flash chromatography, eluted with a gradient of ethyl acetate and cyclohexane to give methyl 4-[[5-(5-methyl-1,2,4-oxadiazol-3-yl)-2-pyridyl]amino]-4-oxo-butanoate A75 (0.062 g, 37% yield). LC-MS (Method F) RT 0.72, 291 (M+H+).

Workup

  1. customThe residue was partitioned between ethyl acetate and water
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. customThe combined organic layer was dried on magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography
  7. washeluted with a gradient of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-028eb5b0f41a4b04b025e9e2f5cb94f7
Source dataset
uspto-grants-2016_05
Patent number
US09345244B2

Reaction notes

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