反应详情

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.

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)