Potassium Carbonate → 5-{[(2,4-Dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-2-phenyl-thiazole-4-carboxylic acid ethyl ester

HRID 642316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642316
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:9][C:10]=1[CH2:11]Br)=[O:5])[CH3:2].[CH2:19]([O:21][C:22](=[O:36])[CH2:23][NH:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:9][C:10]=1[CH2:11][N:24]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:36])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 68428666HCID 68428666, Verbindung

Produkt 1

HCID 684290685-{[(2,4-Dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-2-phenyl-thiazole-4-carboxylic acid ethyl esterAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-bromomethyl-2-phenyl-thiazole-4-carboxylic acid ethyl ester (596 mg, 1.83 mmol), (2,4-dimethoxy-benzylamino)-acetic acid ethyl ester (511 mg, 2.02 mmol) and potassium carbonate (380 mg, 2.75 mmol) in anhydrous dimethylformamide (7 mL) was stirred at room temperature for 20 h before it was quenched with water, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a white solid (562 mg): MS: (+) m/z 521.1 (M+Na+).

Aufarbeitung

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-12837dc7148041768cc80da579d8eb38
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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