Water → HCID 66733865, compound

To a yellow solution of 4,5-diiodo-2-isopropyl-1H-imidazole (10.000 g; 27.629 mmol) in anhydrous DMF (140 ml) was added portionwise, at rt, 55-65% sodium hydride moistened with oil (1.326 g; 33.154 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 (6.810 g; 30.391 mmol) in anhydrous DMF (100 ml) was added dropwise, over 1 h, with an addition funnel. After completion of the addition, the resulting mixture was further heated at 100° C. for 1 h30. The reaction mixture was cooled to 0° C., and water (300 ml) was added slowly. This mixture was extracted with ether (5×150 ml). The combined organic layers were washed with brine (100 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give an orange oil. The crude was purified by FC (DCM/MeOH=30/1) to give the pure product [2-(4,5-diiodo-2-isopropyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester as a yellow solid which was further dried under HV (9.720 g; 70%). LC-MS: tR=0.82 min.; [M+H]+=506.32 g/mol.

1. temperatureThe mixture was then heated to 100° C.
2. additionAfter completion of the addition
3. temperaturethe resulting mixture was further heated at 100° C. for 1 h30
4. temperatureThe reaction mixture was cooled to 0° C.
5. extractionThis mixture was extracted with ether (5×150 ml)
6. washThe combined organic layers were washed with brine (100 ml)
7. dry with materialdried over anh. MgSO4
8. filtrationfiltered
9. concentrationconcentrated to dryness under reduced pressure
10. customto give an orange oil
11. customThe crude was purified by FC (DCM/MeOH=30/1)

ORD record

ord-f8dd5baf83fb4dc3bad1c6698de2a3f8

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188082B2