Hydrochloric Acid → HCID 178442459, Verbindung

HRID 1881440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881440
Cl.[CH3:2][C:3]([CH3:35])([CH2:33][CH3:34])[CH2:4][C:5]1[N:6]=[C:7]([C:16]([OH:32])([CH3:31])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=3)=[CH:20][CH:19]=2)[N:8](S(N(C)C)(=O)=O)[CH:9]=1>CO>[CH3:2][C:3]([CH3:35])([CH2:33][CH3:34])[CH2:4][C:5]1[N:6]=[C:7]([C:16]([OH:32])([CH3:31])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][N:25]=3)=[CH:20][CH:19]=2)[NH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 66705641HCID 66705641, Verbindung

Produkt 1

HCID 178442459HCID 178442459, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Hydrogen chloride (4 M in 1,4-dioxane) (2 mL, 8 mmol) was added to an ambient temperature solution of 4-(2,2-dimethylbutyl)-2-{2-[4-(5-fluoropyridin-2-yl)phenyl]-1-hydroxy-1-methylethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (192 mg, 0.39 mmol) in methanol (4 mL). After stirring at 70° C. for 1 h, volatiles were removed in vacuo. The residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-100% acetone/methylene chloride afforded the title compound. Chiral HPLC eluting with IPA/heptane afforded the two individual enantiomers. 1H NMR (500 MHz, CD3OD) δ 8.47 (s, 1H), 7.82 (m, 1H), 7.73 (d, J=7 Hz, 2H), 7.64 (m, 1H), 7.07 (d, J=7 Hz, 2H), 6.58 (s, 1H), 3.19 (d, J=11 Hz, 1H), 3.13 (d, J=11 Hz, 1H), 2.40 (s, 2H), 1.61 (s, 3H), 1.62 (q, J=5.5 Hz, 2H), 0.87-0.75 (m, 9H); (M+H) found: 382.

Aufarbeitung

  1. customvolatiles were removed in vacuo
  2. customThe residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72a21baffb5549b7a25e8a20c068d2ac
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318767B2

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