Triethylamine → Cyclopropanecarboxylic acid-4-[2-(4-chloro-phenyl)-5-ethyl-thiazol-4-yl]-5-oxo-10-oxa-tricyclo[5.2.1.0*2,6*]dec-3-en-3-yl ester

HRID 41688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41688
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:25][CH3:26])=[C:11]([CH:13]3[C:21](=[O:22])[CH:20]4[CH:15]([CH:16]5[O:23][CH:19]4[CH2:18][CH2:17]5)[C:14]3=[O:24])[N:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:34]1([C:37](Cl)=[O:38])[CH2:36][CH2:35]1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:25][CH3:26])=[C:11]([C:13]3[C:14](=[O:24])[CH:15]4[CH:20]([CH:19]5[O:23][CH:16]4[CH2:17][CH2:18]5)[C:21]=3[O:22][C:37]([CH:34]3[CH2:36][CH2:35]3)=[O:38])[N:12]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 68567518HCID 68567518, Verbindung

Produkt 1

HCID 68568642Cyclopropanecarboxylic acid-4-[2-(4-chloro-phenyl)-5-ethyl-thiazol-4-yl]-5-oxo-10-oxa-tricyclo[5.2.1.0*2,6*]dec-3-en-3-yl esterAusbeute 124,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(4-chloro-phenyl)-5-ethyl-thiazol-4-yl]-10-oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione (100 mg, 0.18 mmol) in DCM (5 ml) and triethylamine (140 μl, 1 mmol) is added the cyclopropane carbonyl chloride (91 μl, 1 mmol) at room temperature. The reaction mixture is stirred overnight at room temperature. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give cyclopropanecarboxylic acid-4-[2-(4-chloro-phenyl)-5-ethyl-thiazol-4-yl]-5-oxo-10-oxa-tricyclo[5.2.1.0*2,6*]dec-3-en-3-yl ester (102 mg).

Aufarbeitung

  1. additionSilica gel is added to the crude
  2. customreaction mixture
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue is purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5d9a184138c2438da5b83b3ab443b92b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530667B2

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