Cyclopentanecarbonyl chloride → (2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-cyclopentylethanone

HRID 448074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448074
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[CH3:13])[CH2:3][CH2:4][CH3:5].[CH:14]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C1C=CN=CC=1)C>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:19]([CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:20])[CH2:3][CH2:4][CH3:5]

Komponenten

4

Edukt 2

HCID 78284Cyclopentanecarbonyl chlorideHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

Produkt 1

HCID 69188133(2Z)-2-(3-butyl-4,5-dimethyl-1,3-thiazol-2(3H)-ylidene)-1-cyclopentylethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Versuchsvorschrift

In a 20 mL vial 3-butyl-2,4,5-trimethylthiazol-3-ium iodide (48 mg in 0.5 mL DMA, 0.16 mmol, 1 equiv.) was added, followed by TEA (38 mg in 0.5 mL DMA, 0.37 mmol, 2.4 equiv.) and the solution went black. DMAP (2 mg in 0.5 mL DMA, 0.016 mmol, 0.1 equiv) was added next, followed by cyclopentanecarbonyl chloride (0.9 mL of 0.2M in DMA, 1.2 equiv). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.88-0.97 (m, 3 H) 1.30-1.39 (m, 2 H) 1.51-1.62 (m, 4 H) 1.62-1.70 (m, 3 H) 1.77-1.87 (m, 2 H) 2.16-2.26 (m, 5 H) 2.73-2.86 (m, 1 H) 3.71-3.83 (m, 4 H) 5.84-5.94 (m, 1 H); MS (ESI) m/z 280 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f4b71200f4094190830905d60b361090
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481574B2

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