Ethyl Acetate → HCID 71279289, compound

HRID 1621112Notes

Reaction equation

HRID 1621112 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][O:31][CH3:32].C(OCC)(=O)C>CN(C=O)C>[CH3:32][O:31][CH2:30][CH2:29][N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[C:9]1[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium Carbonate2×HCID 809722-Bromoethyl methyl ether2×HCID 178453346HCID 178453346, compound

Product 1

HCID 71279289HCID 71279289, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of tert-butyl 2-(4-phenyl-1H-imidazol-2-yl)ethylcarbamate (400 mg, 1.39 mmol, prepared according to example 7, steps 1-2) and potassium carbonate (423 mg, 3.06 mmol) in DMF (4 mL) was stirred for 30 min at RT. After cooling to 0-5° C., 1-bromo-2-methoxyethane (157 μL, 1.67 mmol) was added. The ice bath was removed after 5 min and the reaction mixture was stirred at RT for 16 h. Another two equivalents of both potassium carbonate (618 mg, 4.45 mmol) and 1-bromo-2-methoxyethane (262 μL, 2.78 mmol) were added at RT and the reaction mixture was heated to 60° C. and stirred for 20 h. The reaction mixture was poured into ethyl acetate (50 mL) and the organic phase was washed with water (3×20 mL) and brine (25 mL). The aqueous layers were back-extracted with ethyl acetate (50 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as colorless solid (359 mg, 1.04 mmol, 74.7%). MS: M=346.2 (M+H)+

Workup

  1. temperatureAfter cooling to 0-5° C.
  2. customThe ice bath was removed after 5 min
  3. stirringthe reaction mixture was stirred at RT for 16 h
  4. temperaturethe reaction mixture was heated to 60° C.
  5. stirringstirred for 20 h
  6. washthe organic phase was washed with water (3×20 mL) and brine (25 mL)
  7. extractionThe aqueous layers were back-extracted with ethyl acetate (50 mL)
  8. dry with materialThe organic layers were dried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe product was obtained
  11. customafter purification by flash chromatography (

Sources & evidence

ORD record
ord-e4dbb856cf8d451dbcb608db1214d026
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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