Cesium carbonate → 2-[3-(3-Methoxy-phenyl)-propoxy]-4-methyl-thiazole-5-carboxylic acid ethyl ester

HRID 1952545

Reaktionsgleichung

Reaktionsgleichung von HRID 1952545
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][O:12]S(C)(=O)=O)[CH:6]=[CH:7][CH:8]=1.[CH2:17]([O:19][C:20]([C:22]1[S:26][C:25](=O)[NH:24][C:23]=1[CH3:28])=[O:21])[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:17]([O:19][C:20]([C:22]1[S:26][C:25]([O:12][CH2:11][CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:24][C:23]=1[CH3:28])=[O:21])[CH3:18]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 11074139Ethyl 2-hydroxy-4-methyl-1,3-thiazole-5-carboxylateHCID 23150769HCID 23150769, Verbindung

Produkt 1

HCID 682267072-[3-(3-Methoxy-phenyl)-propoxy]-4-methyl-thiazole-5-carboxylic acid ethyl esterAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of methanesulfonic acid 3-(3-methoxy-phenyl)-propyl ester (1.20 g, 4.912 mmol), 4-Methyl-2-oxo-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester (0.960 g, 5.128 mmol) and cesium carbonate (3.2 hm, 9.82 mmol) in anhydrous DMF was heated to oil bath at 75° C. for 2.5 h. The reaction mixture was cooled, concentrated and diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The organic layers were washed with 2N HCl (30 mL), water ((30 mL), brine (30 mL), dried over magnesium sulphate, filtered and concentrated to give a brown oil. The crude product is purified by flash column chromatography (10%-30% EtOAc in hexane) to give 2-[3-(3-Methoxy-phenyl)-propoxy]-4-methyl-thiazole-5-carboxylic acid ethyl ester (0.84 g, 51%) as a yellow oil. MS m/e 336.4 (M+H+).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. additiondiluted with water (50 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe organic layers were washed with 2N HCl (30 mL), water ((30 mL), brine (30 mL)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a brown oil
  10. customThe crude product is purified by flash column chromatography (10%-30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a262299de41c490d8c31264da3a66eb0
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404859B2

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