Ammonium Acetate → 1-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridin-3-yl]-2-methylpropane-1,2-diol

HRID 1882014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882014
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[C:14](=O)[CH2:15][CH:16]([CH3:31])[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH:25]([OH:30])[C:26]([OH:29])([CH3:28])[CH3:27])=[CH:21][N:20]=3)=O)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:44]>C(O)(=O)C.C(OCC)(=O)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14]3[NH:44][C:17]([C:19]4[N:20]=[CH:21][C:22]([CH:25]([OH:30])[C:26]([CH3:27])([OH:29])[CH3:28])=[CH:23][CH:24]=4)=[C:16]([CH3:31])[CH:15]=3)[CH2:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 517165Ammonium AcetateHCID 593314295-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Produkt 1

HCID 593316081-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridin-3-yl]-2-methylpropane-1,2-diolAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (235 mg) in acetic acid (5 mL) was added ammonium acetate (519 mg), and the mixture was stirred at 90° C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (150 mg, yield 66%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate. MS: 539 (MH+).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f0fb6e860efd480fba805a4924d6eda1
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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