Sodium Hydroxide → 2-(5-[1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)-5-[(2-methoxyethoxy)methyl]-1,3-thiazole

HRID 1882055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882055
[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]([CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])=[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]([CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:22][N:23]=4)=[CH:16][CH:15]=3)[CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 593314355-[4-(cyclopropylsulfonyl)phenyl]-1-[5-[(2-methoxyethoxy)methyl]-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Produkt 1

HCID 593313802-(5-[1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)-5-[(2-methoxyethoxy)methyl]-1,3-thiazoleAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-[(2-methoxyethoxy)methyl]-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (0.52 g), ammonium acetate (0.55 g) and acetic acid (6 mL) was stirred at 100° C. for 2 hr. The reaction mixture was neutralized with 8M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (0.47 g, yield 94%) was obtained as a yellow resin from a fraction eluted with tetrahydrofuran-hexane (1:4, volume ratio). MS: 531 (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-3ff0f4df41e141dcbdc3f89205dce3e3
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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