Imidazole → HCID 67958930, compound

HRID 527238Notes

Reaction equation

HRID 527238 reaction equation
N#N.[OH:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1.N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].[NH4+].[Cl-]>C1COCC1.CC(=O)OCC>[Si:19]([O:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 947NitrogenHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 67281821HCID 67281821, compound

Product 1

HCID 67958930HCID 67958930, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-(hydroxymethyl)oxazole-4-carboxylate (12.00 g, 76.37 mmol) in THF (360 mL) was treated with imidazole (10.40 g, 152.75 mmol) followed by tert-butyldimethylsilyl chloride (23.02 g, 152.75 mmol) and the resulting mixture was stirred at rt for 2.5 h. EA (360 mL) and sat. aq. NH4Cl (360 mL) were added. The layers were separated and the aq. layer was extracted with EA (360 mL). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (7:3 hept-EA) gave the title compound as a white solid: TLC: rf (7:3 hept-EA)=0.44. LC-MS-conditions 06: tR=0.98 min, [M+H]+=272.38.

Workup

  1. customThe layers were separated
  2. extractionthe aq. layer was extracted with EA (360 mL)
  3. dry with materiallayers were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (7:3 hept-EA)

Sources & evidence

ORD record
ord-8083e17217704bcea2c1d88f7fa0e886
Source dataset
uspto-grants-2016_05
Patent number
US09346793B2

Reaction notes

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