Water → Diethyl 2-acetoxymethyl-1-benzylimidazole-4,5-dicarboxylate

HRID 265199Notes

Reaction equation

[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[CH2:6]([N:13]1[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[NH:15][C:14]1([CH3:29])Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.O>CN(C)C=O>[C:1]([O:4][CH2:29][C:14]1[N:13]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:15]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

1.11 g of sodium acetate were added to a solution of 2.67 g of diethyl 1-benzyl-2-bromomethylimidazole-4,5-dicarboxylate [prepared as described in Preparation 42(ii)] in 30 ml of dimethylformamide, and the resulting mixture was heated at 40° C. for 5 hours. At the end of this time, the reaction solution was mixed with ethyl acetate and water, and then the ethyl acetate layer was separated. The resulting ethyl acetate extract was washed with an aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.52 g of the title compound as a syrup.

Workup

customthe ethyl acetate layer was separated
extractionThe resulting ethyl acetate extract
washwas washed with an aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
customThe solvent was then removed by distillation under reduced pressure
customThe residue was purified by column chromatography through silica gel
additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-9182ce1639a7418f994ca27831807a13
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646171

Reaction notes

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