Hydrochloric Acid → 1-[4-(2,2-dimethylpropyl)-1H-imidazol-2-yl]-2-(4-pyridin-2-ylphenyl)ethanol

HRID 425336Notes

Reaction equation

Cl.[CH3:2][C:3]([CH3:32])([CH3:31])[CH2:4][C:5]1[N:6]=[C:7]([CH:16]([OH:30])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:20][CH:19]=2)[N:8](S(N(C)C)(=O)=O)[CH:9]=1>O1CCCC1>[CH3:2][C:3]([CH3:32])([CH3:31])[CH2:4][C:5]1[N:6]=[C:7]([CH:16]([OH:30])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:20][CH:19]=2)[NH:8][CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1.5 N Hydrochloric acid (1 mL) was added to an ambient temperature solution of 4-(2,2-dimethylpropyl)-2-[1-hydroxy-2-(4-pyridin-2-ylphenyl)ethyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide (7 mg, 0.02 mmol) in tetrahydrofuran (1 mL). After heating in a sealed tube at 70° C. until no further reaction (LCMS), the reaction mixture was cooled to 0° C., quenched with 10% aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Preparative plate chromatography eluting with 15% methanol/ethyl acetate afforded the title compound. High pressure liquid chromatography (Chiralcel OD column) eluting with 20% isopropanol/heptane afforded the two pure enantiomers. (M+H) found: 336.

Workup

temperaturethe reaction mixture was cooled to 0° C.
customquenched with 10% aqueous sodium hydroxide
extractionextracted with ethyl acetate
dry with materialThe combined organic extracts were dried (magnesium sulfate)
concentrationconcentrated in vacuo
washPreparative plate chromatography eluting with 15% methanol/ethyl acetate

Sources & evidence

ORD record: ord-1c852006dfaf47faba60384fce73db93
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Reaction notes

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