Methanol → 2-(4-methanesulfonyl-phenyl)-3-[2-(tetrahydropyran-2-yloxy)-cyclopentyl]-N-thiazol-2-yl-propionamide

HRID 2214069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214069
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C[O:8][C:9](=O)[CH:10]([C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1)[CH2:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH:13]1[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1.C[O-].[Mg+2].C[O-].CO>>[CH3:33][S:30]([C:27]1[CH:26]=[CH:25][C:24]([CH:10]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:9]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[O:8])=[CH:29][CH:28]=1)(=[O:32])=[O:31]

Komponenten

5

Edukt 4

HCID 887MethanolHCID 21552-AminothiazoleHCID 164537Methanol, magnesium salt (2:1)HCID 674821442-(4-Methanesulfonyl-phenyl)-3-[2-(tetrahydropyran-2-yloxy)-cyclopentyl]-propionic acid methyl ester

Produkt 1

HCID 219590442-(4-methanesulfonyl-phenyl)-3-[2-(tetrahydropyran-2-yloxy)-cyclopentyl]-N-thiazol-2-yl-propionamideAusbeute 38 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2-Aminothiazole (314.3 mg, 3.14 mmol) and 2-(4-methanesulfonyl-phenyl)-3-[2-(tetrahydropyran-2-yloxy)-cyclopentyl]-propionic acid methyl ester (859.2 g, 2.09 mmol) were treated with a solution of magnesium methoxide in methanol (7.4 wt. %, 12 mL, 8.37 mmol). The resulting reaction mixture was heated under reflux for 24 h. The reaction mixture was allowed to cool to 25° C. and then filtered through a pad of celite. The pad of celite was washed well with ethyl acetate until the washings indicated the absence of product by thin layer chromatography. The filtrate was then washed with a 10% aqueous hydrochloric acid solution (3×100 mL). The organic layer was then dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 1/1 hexanes/ethyl acetate) afforded 2-(4-methanesulfonyl-phenyl)-3-[2-(tetrahydropyran-2-yloxy)-cyclopentyl]-N-thiazol-2-yl-propionamide (377.4 mg, 38%) as a yellow oil: EI-HRMS m/e calcd for C23H30N2O5S2 (M+) 478.1596, found 478.1604.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 24 h
  4. filtrationfiltered through a pad of celite
  5. washThe pad of celite was washed well with ethyl acetate until the washings
  6. washThe filtrate was then washed with a 10% aqueous hydrochloric acid solution (3×100 mL)
  7. dry with materialThe organic layer was then dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bcbf2cfbc34c48a8a50576c7d1e8c606
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105671B2

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