Imidazole → HCID 86748544, compound

HRID 1282259Notes

Reaction equation

HRID 1282259 reaction equation
C([O:4][C@H:5]1[C@@H:8]([CH:9]=[C:10]([CH3:12])[CH3:11])[NH:7][C:6]1=[O:13])(=O)C.C([O-])([O-])=O.[K+].[K+].N1C=CN=C1.[CH2:25]([Si:27](Cl)([CH2:30][CH3:31])[CH2:28][CH3:29])[CH3:26]>CO>[CH2:25]([Si:27]([CH2:30][CH3:31])([CH2:28][CH3:29])[O:4][C@H:5]1[C@@H:8]([CH:9]=[C:10]([CH3:11])[CH3:12])[NH:7][C:6]1=[O:13])[CH3:26]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 13819ChlorotriethylsilaneHCID 86748545HCID 86748545, compound

Product 1

HCID 86748544HCID 86748544, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

(±)-cis-3-Acetyloxy-4-isobutenylazetidin-2-one (1.47 g, 8.0 mmol) was dissolved in methanol (15 mL) and was stirred with K2CO3 (110.5 mg, 0.8 mmol) for 3 h at ambient temperature. The solution was then neutralized with Dowex 50W-X8resin and then filtered. The filtrate was concentrated and the crude solid was dissolved in THF (25 mL) and cooled to 5° C. in an ice bath. Imidazole (544.0 mg, 8.0 mmol) was added and once dissolved, triethylsilyl chloride (1.34 mL, 8.0 mmol) was added dropwise via syringe. The resulting slurry was allowed to warm to ambient temperature and stir overnight. The solution was filtered and the filtrate was washed with water, then brine. The organic fraction was dried (MgSO4) and concentrated. The crude solid was purified by silica gel chromatography (eluted with hexanes/ethyl acetate 3:1) to furnish the desired product (612 mg, 30%) as a pale yellow solid; 1H NMR (300 MHz, CDCl3): δ 5.87. (bs, 1H), 5.31-5.26 (m, 1H), 4.90 (dd, 1H, J=2.2, 4.7 Hz), 4.42 (dd, 1H, J=4.7, 9.3 Hz), 1.74 (s, 3H), 1.28 (s, 3H), 0.98-0.91 (m, 9H), 0.71-0.55 (m, 6H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe crude solid was dissolved in THF (25 mL)
  4. dissolutiononce dissolved
  5. temperatureto warm to ambient temperature
  6. filtrationThe solution was filtered
  7. washthe filtrate was washed with water
  8. dry with materialThe organic fraction was dried (MgSO4)
  9. concentrationconcentrated
  10. customThe crude solid was purified by silica gel chromatography (eluted with hexanes/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-aa9186374d7e4e2ab5ce06a7905863b5
Source dataset
uspto-grants-2002_09
Patent number
US06455575B2

Reaction notes

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