Dichloromethane → tert-Butyl [(1S)-2-(3-bromo-4-iodophenyl)-1-(5-phenyl-1-[2-(trimethylsilyl)ethoxy]methyl-1H-imidazol-2-yl)ethyl]carbamate

HRID 724725Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:11]2[NH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[I:8].[CH3:30][Si:31]([CH3:38])([CH3:37])[CH2:32][CH2:33][O:34][CH2:35]Cl.C(N(CC)C(C)C)(C)C.C(Cl)Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27])[C:11]2[N:12]([CH2:35][O:34][CH2:33][CH2:32][Si:31]([CH3:38])([CH3:37])[CH3:30])[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[I:8]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of tert-butyl [(1S)-2-(3-bromo-4-iodophenyl)-1-(5-phenyl-1H-imidazol-2-yl)ethyl]carbamate (950 mg, 836 μmol), [β-(trimethylsilyl)ethoxy]methyl chloride (163 μL, 919 μmol), N,N-diisopropylethylamine (582 μL) and methylene chloride (8.91 mL) was stirred at 0° C. for 60 min and stirred at 25° C. for 2 h. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (432 mg, 59%). MF=C28H37BrIN3O3Si; LCMS found for C28H38BrIN3O3Si (M+H)+: m/z=698.

Workup

extractionextracted with ethyl acetate three times
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-66de0ae7d6a446be99d9a4b64d149211
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

Loading…