Water → 3-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propionic acid methyl ester

HRID 220262Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5](=[O:25])[CH2:6][CH2:7][C:8]1[NH:9][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1.[CH3:26][Si:27]([CH2:30][CH2:31][O:32][CH2:33]Cl)([CH3:29])[CH3:28].O>CN(C=O)C>[CH3:3][O:4][C:5](=[O:25])[CH2:6][CH2:7][C:8]1[N:12]([CH2:33][O:32][CH2:31][CH2:30][Si:27]([CH3:29])([CH3:28])[CH3:26])[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

47 mg of sodium hydride were added portionwise to a solution of 300 mg of 3-(4,5-diphenyl-1H-imidazol-2-yl)-propionic acid methyl ester in 2 mL of anh. DMF at 0° C. The mixture was stirred for 1 h at 0° C. then 179 mg of SEM-Cl were added dropwise at 0° C. The reaction mixture was allowed to warm up to rt, stirred for 1 h then poured into water and extracted with Et2O. The organic phase was washed with water/brine, dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using heptane/EtOAc from 88/12 to 0/100 as eluant to yield 308 mg of 3-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propionic acid methyl ester as a yellowish oil.

Workup

temperatureto warm up to rt
stirringstirred for 1 h
extractionextracted with Et2O
washThe organic phase was washed with water/brine
dry with materialdried over anh. Na2SO4
concentrationconcentrated in vacuo
customThe resulting crude material was purified by CC

Sources & evidence

ORD record: ord-f48b4118b5714c2f8b5d339655edf7e5
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202885B2

Reaction notes

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