Water → [2-(4,5-Diiodo-2-methoxymethylimidazol-1-yl)ethyl]carbamic acid tert-butyl ester

HRID 1929641Notes

Reaction equation

HRID 1929641 reaction equation
[I:1][C:2]1[N:3]=[C:4]([CH2:8][O:9][CH3:10])[NH:5][C:6]=1[I:7].[H-].[Na+].[C:13]([NH:20][CH2:21][CH2:22]Br)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O>CN(C=O)C>[C:16]([O:15][C:13](=[O:14])[NH:20][CH2:21][CH2:22][N:3]1[C:2]([I:1])=[C:6]([I:7])[N:5]=[C:4]1[CH2:8][O:9][CH3:10])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 667340334,5-diiodo-2-methoxymethyl-1H-imidazole

Product 1

HCID 66734234[2-(4,5-Diiodo-2-methoxymethylimidazol-1-yl)ethyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4,5-diiodo-2-methoxymethyl-1H-imidazole (3.000 g; 8.244 mmol) in anhydrous DMF (35 ml) was added portionwise, at rt, 55-65% sodium hydride moistened with oil (395 mg; 9.895 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 20 min. The mixture was then heated to 100° C., and a colorless homogeneous solution of 2-(Boc-amino)-ethylbromide (2.032 g; 9.068 mmol) in anhydrous DMF (30 ml) was added dropwise, over 15 min., with an addition funnel. After completion of the addition, the resulting dark-orange homogeneous mixture was further heated at 100° C. for 1 h45. The reaction mixture was cooled to rt, and water (175 ml) was added slowly. This mixture was extracted with ether (4×120 ml). The combined organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM/MeOH=50/1) to give the pure product [2-(4,5-diiodo-2-methoxymethyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butylester as a pale yellow solid which was further dried under HV (3.050 g; 73%). LC-MS: tR=0.87 min.; [M+H]+=508.16 g/mol.

Workup

  1. temperatureThe mixture was then heated to 100° C.
  2. additionAfter completion of the addition
  3. temperaturethe resulting dark-orange homogeneous mixture was further heated at 100° C. for 1 h45
  4. temperatureThe reaction mixture was cooled to rt
  5. extractionThis mixture was extracted with ether (4×120 ml)
  6. dry with materialThe combined organic layers were dried over anh. MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe crude was purified by FC (DCM/MeOH=50/1)

Sources & evidence

ORD record
ord-7cd16dcd98c34fceae515f636c26a392
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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