1-(1H-Imidazol-1-yl)ethanone → HCID 86657028, compound

HRID 1909114Notes

Reaction equation

HRID 1909114 reaction equation
[NH2:1]/[C:2](=[N:16]\[OH:17])/[C@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].[C:18](N1C=CN=C1)(=O)[CH3:19]>O1CCOCC1>[CH3:18][C:19]1[O:17][N:16]=[C:2]([C@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:4])[N:1]=1

Participants

4

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 140555601HCID 140555601, compound

Product 1

HCID 86657028HCID 86657028, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of benzyl [(1R,2Z)-2-amino-2-(hydroxyimino)-1-methylethyl]carbamate (2.25 g, 9.48 mmol) in dioxane (80 ml) was added 1-acetyl-1H-imidazole (3.13 g, 28.5 mmol) and the mixture heated to 90° C. After 16 h, the solution was concentrated and the residue was dissolved in 200 mL of dichloromethane. The mixture was washed with 100 mL of aqueous saturated sodium bicarbonate (2×) and brine (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) to give the title compound (1.1 g). MS 262.1 (M+1).

Workup

  1. concentrationthe solution was concentrated
  2. dissolutionthe residue was dissolved in 200 mL of dichloromethane
  3. washThe mixture was washed with 100 mL of aqueous saturated sodium bicarbonate (2×) and brine (100 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-069bd8ff3eb64518a2907b57ac52a533
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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