Imidazole → HCID 54282809, compound

HRID 1004623Notes

Reaction equation

HRID 1004623 reaction equation
[H][H].[Si]([O:10][C@H:11]([C@H:14]1[C@@H:17]([CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[S:20])[NH:16][C:15]1=[O:27])[CH2:12][CH3:13])(C(C)(C)C)(C)C.N1C=CN=C1.[CH2:33]([Si:35](Cl)([CH2:38][CH3:39])[CH2:36][CH3:37])[CH3:34]>C(#N)C.C(OCC)(=O)C.CN(C)C=O>[CH2:33]([Si:35]([CH2:38][CH3:39])([CH2:36][CH3:37])[O:10][C@H:11]([C@H:14]1[C@@H:17]([CH2:18][C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[S:20])[NH:16][C:15]1=[O:27])[CH2:12][CH3:13])[CH3:34]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 53822480HCID 53822480, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54282809HCID 54282809, compoundYield 69.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

An aqueous solution of hydrogen fluroride (46%, 2.53 ml) was added to a solution of the compound (2.29 g, 5.8 mmol) prepared in Example 7 in acetonitrile (40 ml) at room temperature in an argon atmosphere. After stirring for two hours at this temperature, the mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a de-protected compound as an oily substance. Imidazole (579 mg, 8.5 mmol) and triethylsilyl chloride (1.24 ml, 7.4 mmol) were added to the solution of this de-protected compound in N,N-dimethylformamide (10 ml) at room temperature, followed by stirring for 10 minutes at the same temperature. After the reaction, the reaction mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of potassium hydrogen sulfate, a saturated aqueous solution of sodium hydrogencarbonate, and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1), to obtain 1.52 g (yield 67%) of the title compound as a light yellow oily substance.

Workup

  1. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine in this order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customto obtain a de-protected compound as an oily substance
  5. stirringby stirring for 10 minutes at the same temperature
  6. customAfter the reaction
  7. washwashed with a saturated aqueous solution of potassium hydrogen sulfate
  8. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, and saturated brine in this order, and dried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-f0b3be6ece154e04adc01bf58686c796
Source dataset
uspto-grants-2000_04
Patent number
US06051569

Reaction notes

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