Potassium Carbonate → (S)-tert-butyl 1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethylcarbamate

HRID 1506620Notes

Reaction equation

HRID 1506620 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@@H:6]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[O:30][CH3:31].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH3:31][O:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C@@H:6]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 403081-(Bromomethyl)-2-methoxybenzeneHCID 57976325[(S)-1-(1H-imidazol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 90281194(S)-tert-butyl 1-(1-(2-methoxybenzyl)-1H-imidazol-2-yl)-2-phenylethylcarbamate

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To (S)-tert-butyl 1-(1H-imidazol-2-yl)-2-phenylethylcarbamate (120 mg, 0.42 mmol) in DMF (1 mL) was added 1-(bromomethyl)-2-methoxybenzene (58 μL, 0.42 mmol), K2CO3 (70 mg, 0.5 mmol) and TBAI (5 mg) and heated to 90° C. After stirring for 1 hr and cooling to ambient temperature, the reaction was partitioned between EtOAc and H2O. The organics were separated, washed with saturated aqueous NaHCO3, and saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide the desired product: MS (m/z) 408.2 [M+H]+.

Workup

  1. temperaturecooling to ambient temperature
  2. customthe reaction was partitioned between EtOAc and H2O
  3. customThe organics were separated
  4. washwashed with saturated aqueous NaHCO3, and saturated aqueous NaCl
  5. customSolvents were removed in vacuo
  6. customthe residue purified by column chromatography on silica

Sources & evidence

ORD record
ord-a5fcf6e01eb2447f9ae137cffe635255
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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