Potassium Carbonate → 3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acrylic Acid Ethyl Ester

HRID 11682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11682
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=O)[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][CH:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][CH:13]2[CH3:27])=[O:11])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:36]([O-:39])(=[O:38])[CH3:37].[CH2:40]([PH+](CC)CC)[CH3:41]>C(O)C.O>[CH2:40]([O:38][C:36](=[O:39])[CH:37]=[CH:28][C:4]1[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][C@H:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][C@H:13]2[CH3:27])=[O:11])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:41]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 219733105-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehydeHCID 21973468Triethylphosphonium acetate

Produkt 1

HCID 696553743-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acrylic Acid Ethyl EsterAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a 0° C. solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehyde (0.200 g, 0.47 mmol) in ethanol (5 mL) was added potassium carbonate (0.131 g, 0.95 mmol) in water (0.30 mL) and triethyl phosphonium acetate (0.21 g, 0.19 mL). The reaction mixture was warmed to room temperature over 48 hours, filtered through celite, the filter cake was washed with ethanol and concentrated in vacuo. Purification via chromatography on silica gel gave the title compound (0.102 g).

Aufarbeitung

  1. filtrationfiltered through celite
  2. washthe filter cake was washed with ethanol
  3. concentrationconcentrated in vacuo
  4. customPurification via chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-749a9b298e704c3cbd3759170ce98838
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

Notizen zur Reaktion

Wird geladen…