Sodium Hydroxide → 1-[2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]-2,2,2-trifluoroethanol

HRID 1882062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882062
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)[C:14](=O)[CH2:15][CH2:16][C:17]([C:19]3[S:20][C:21]([CH:24]([OH:29])[C:25]([F:28])([F:27])[F:26])=[CH:22][N:23]=3)=O)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:42].[OH-].[Na+]>C(O)(=O)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14]3[NH:42][C:17]([C:19]4[S:20][C:21]([CH:24]([OH:29])[C:25]([F:28])([F:26])[F:27])=[CH:22][N:23]=4)=[CH:16][CH:15]=3)[CH2:31][CH:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 593315505-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)-1-[5-(2,2,2-trifluoro-1-hydroxyethyl)-1,3-thiazol-2-yl]hexane-1,4-dione

Produkt 1

HCID 593315431-[2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]-2,2,2-trifluoroethanolAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)-1-[5-(2,2,2-trifluoro-1-hydroxyethyl)-1,3-thiazol-2-yl]hexane-1,4-dione (0.45 g), ammonium acetate (0.31 g) and acetic acid (6 mL) was stirred at 80° C. for 3 hr. The reaction mixture was neutralized with 8M sodium hydroxide, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to basic silica gel column chromatography, and the title compound (0.28, yield 65%) was obtained as a yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio). MS: 541 (MH+).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-58e3cad793e84327942bdc5ec3a55469
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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