Diethyl Ether → (S)-3-chloro-N-(4-hydroxy-1-(4-(2-(1-(hydroxyimino)ethyl)-1-methyl-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamide

HRID 1436207Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[O:33][CH:34]([CH3:36])[CH3:35])[C:5]([NH:7][C@H:8]([CH2:27][CH2:28][OH:29])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:17]=[C:18]([C:22](=[N:24][O:25]C)[CH3:23])[N:19]([CH3:21])[CH:20]=2)=[CH:12][CH:11]=1)=[O:6].C[Mg+].[Br-].CCOCC>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[O:33][CH:34]([CH3:36])[CH3:35])[C:5]([NH:7][C@H:8]([CH2:27][CH2:28][OH:29])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:17]=[C:18]([C:22](=[N:24][OH:25])[CH3:23])[N:19]([CH3:21])[CH:20]=2)=[CH:14][CH:15]=1)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2 (3.7 g, 11.4 mmol) in THF (40 mL) was added dropwise MeMgBr in Et2O (3M, 11.4 ml, 34.2 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min. The solution was quenched by saturated NH4Cl at 0° C. and diluted between EtOAc and H2O. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give 3 (3.0 g, 94%) without further purification. LRMS (M+H+) m/z 279.0.

Workup

customThe solution was quenched by saturated NH4Cl at 0° C.
additiondiluted between EtOAc and H2O
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-f185ec94b20e4529ba92de779da59b05
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618981B2

Reaction notes

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