Sodium hydride → HCID 68427417, Verbindung

HRID 642291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642291
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:18]Br)=[O:5])[CH3:2].[CH2:20]([O:22][C:23](=[O:33])[CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH3:21].[H-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:18][N:25]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:33])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 357729Ethyl 2-((tert-butoxycarbonyl)amino)acetateHCID 58610288HCID 58610288, Verbindung

Produkt 1

HCID 68427417HCID 68427417, VerbindungAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 4-bromomethyl-2-(4-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (2.22 g, 6.18 mmol), tert-butoxycarbonylamino-acetic acid ethyl ester (1.32 g, 6.48 mmol) and sodium hydride (60% in mineral oil, 296 mg, 7.4 mmol) in anhydrous dimethylformamide (30 mL) was stirred at 0° C. for one hour and room temperature for four hours before it was quenched with brine. The mixture was partitioned between ethyl acetate and water. 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 yellow oil (964 mg): 1H NMR (CDCl3, 200 MHz): δ=7.87 (d, 2H), 7.39 (d, 2H), 4.99 (m, 2H), 4.21 (m, 6H), 1.45 (s, 9H), 1.26 (t, 3H).

Aufarbeitung

  1. customwas quenched with brine
  2. customThe mixture was partitioned between ethyl acetate and water
  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-843de80454ca4fa3923b552e7a005a17
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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