Methyl Thioglycolate → HCID 67725929, Verbindung

HRID 52103

Reaktionsgleichung

Reaktionsgleichung von HRID 52103
[H-].[Na+].[C:3]([O:7][CH3:8])(=[O:6])[CH2:4][SH:5].[N:9]1([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][NH:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32]Cl)[CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>O1CCCC1>[N:9]1([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][NH:27][C:28](=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][S:5][CH2:4][C:3]([O:7][CH3:8])=[O:6])[CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 67725907N-[4-(4-Piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-chloropentanamide

Produkt 1

HCID 67725929HCID 67725929, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

344 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling and in an atmosphere of nitrogen, to a solution of 0.35 ml of methyl thioglycolate in 90 ml of tetrahydrofuran, and the resulting mixute was stirred at room temperature for 30 minutes. At the end of this time, it was cooled with ice, and a solution of 2.94 g of N-[4-(4-piperidinomethyl-2-pyridyloxy)-cis-2-butenyl]-5-chloropentanamide [prepared as described in step (a) above] in 30 ml of tetrahydrofuran was added dropwise to the mixture. The reaction mixture was then stirred at room temperature for 2 hours, after which the solvent was removed by distillation under reduced pressure. The residue was mixed with water, and the resulting aqueous mixture was extracted with ethyl acetate. The extract was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:19 by volume mixture of methanol and ethyl acetate as the eluent, to give 2.84 g (yield 89%) of the title compound as an oil.

Aufarbeitung

  1. temperatureAt the end of this time, it was cooled with ice
  2. stirringThe reaction mixture was then stirred at room temperature for 2 hours
  3. customafter which the solvent was removed by distillation under reduced pressure
  4. additionThe residue was mixed with water
  5. extractionthe resulting aqueous mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated by evaporation under reduced pressure
  7. customthe residue was purified by column chromatography through silica gel
  8. additionby volume mixture of methanol and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-22f86299ab3f465e992d776440572a44
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616579

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