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

HRID 1929642Notes

Reaction equation

HRID 1929642 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][O: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][O:18][CH3:19])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 66734234[2-(4,5-Diiodo-2-methoxymethylimidazol-1-yl)ethyl]carbamic acid tert-butyl esterHCID 178461630HCID 178461630, compound2×

Product 1

HCID 66733937[2-(4-Iodo-2-methoxymethylimidazol-1-yl)ethyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of [2-(4,5-diiodo-2-methoxymethyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butylester (3.050 g; 6.015 mmol) in anhydrous THF (30 ml), under nitrogen, was cooled to −40° C., and a solution of 1M EtMgBr in THF (6.02 ml; 6.02 mmol) was then added dropwise over 10 min. After addition, the resulting solution was stirred between −40° C. and −30° C. for 10 min. (conversion=53% according to LC-MS), and additional 1M EtMgBr (3 ml; 3 mmol) was added. Stirring at −40° C. was continued for additional 20 min. (reaction completed). The reaction mixture was then treated with water (2 ml) at −40° C., and was allowed to warm-up to rt. Ether (40 ml) was added, and the resulting solution was washed with water (25 ml) and brine (30 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=50/1) to give the pure product [2-(4-iodo-2-methoxymethyl-imidazol-1-yl)-ethyl]-carbamic acid tert-butyl ester as a yellow solid (1.645 g; 72%). LC-MS: tR=0.70 min.; [M+H]+=382.29 g/mol.

Workup

  1. additionAfter addition
  2. additionwas added
  3. custom(reaction completed)
  4. temperatureto warm-up to rt
  5. washthe resulting solution was washed with water (25 ml) and brine (30 ml)
  6. dry with materialThe organic layer was 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-83ee2f95cea84dba82705a7d46bb590d
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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