Water → [2-(4-Iodo-2-propylimidazol-1-yl)ethyl]carbamic acid tert-butyl ester

HRID 1929638Notes

Reaction equation

HRID 1929638 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][N:10]1[C:14](I)=[C:13]([I:16])[N:12]=[C:11]1[CH2:17][CH2:18][CH3:19])([CH3:4])([CH3:3])[CH3:2].CC[Mg+].[Br-].O.CCOCC>C1COCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([I:16])[N:12]=[C:11]1[CH2:17][CH2:18][CH3:19])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 66733740[2-(4,5-Diiodo-2-propylimidazol-1-yl)ethyl]carbamic acid tert-butyl esterHCID 178461630HCID 178461630, compound2×

Product 1

HCID 66733914[2-(4-Iodo-2-propylimidazol-1-yl)ethyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of [2-(4,5-diiodo-2-propyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (8.690 g; 17.204 mmol) in anhydrous THF (100 ml), under nitrogen, was cooled to −40° C., and a solution of 1M EtMgBr in THF (20.5 ml; 20.5 mmol; 1.2 eq.) was then added dropwise over 15 min. After addition, the resulting solution was stirred between −40° C. and −30° C. for 10 min. (conversion=55% according to LC-MS), and additional 1M EtMgBr in THF (13.9 ml; 13.9 mmol; 0.8 eq.) was added in order to complete the reaction. The reaction mixture was then treated with water (5 ml) at −40° C., and was allowed to warm-up to rt. Ether (200 ml) was added, and the resulting solution was washed with brine (2×200 ml). The organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. The crude was purified by FC (DCM/MeOH=20/1) to give the pure product [2-(4-iodo-2-propyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester as a yellow oil (6.110 g; 94%). LC-MS: tR=0.74 min.; [M+H]+=380.00 g/mol.

Workup

  1. additionAfter addition
  2. additionwas added in order
  3. customthe reaction
  4. washthe resulting solution was washed with brine (2×200 ml)
  5. dry with materialThe organic layer was dried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe crude was purified by FC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-58ce91c2bde744c5b1b5acc2a2feacf7
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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