Acetamidomalonic acid diethyl ester → Diethyl acetamido[(pyridin-4-yl)methyl]propanedioate

HRID 2230024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230024
COC(=O)C([CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)NC(=O)CN(S(C1C=CC(C)=CC=1)(=O)=O)C.[Na].[C:30]([NH:33][CH:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])(=[O:32])[CH3:31].Cl.N1C=CC(CCl)=CC=1>CCO>[N:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:34]([NH:33][C:30](=[O:32])[CH3:31])([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 14041Acetamidomalonic acid diethyl esterHCID 745704-(Chloromethyl)pyridinium chlorideHCID 5360545SodiumHCID 18464215HCID 18464215, Verbindung

Produkt 1

HCID 13817909Diethyl acetamido[(pyridin-4-yl)methyl]propanedioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-(Toluene4-sulfonyl)sarcosyl-β-(pyrid-4-yl)-D,L-alanine methyl ester was employed in this reaction and was prepared as follows. Sodium metal (2 eq.) was dissolved in EtOH containing diethyl acetamidomalonate (1 eq.) and 4-picolylchloride hydrochloride (1 eq.). The mixture was heated to reflux for 6 hr, and then cooled and filtered to remove NaCl (washed with EtOH). The solvent was removed in vacuo and the mixture was taken up into saturated aq NaHCO3 and extracted with EtOAc. The solvent was removed and the residue purified by silica gel flash chromatography (95:5 CH2Cl2/MeOH) to give diethyl 2-(4-pyridylmethyl)-2-acetamidomalonate.

Aufarbeitung

  1. customwas prepared
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 6 hr
  4. temperaturecooled
  5. filtrationfiltered
  6. customto remove NaCl (washed with EtOH)
  7. customThe solvent was removed in vacuo
  8. extractionextracted with EtOAc
  9. customThe solvent was removed
  10. customthe residue purified by silica gel flash chromatography (95:5 CH2Cl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-2e0025cbd5dc4fbea6310f3358748bcd
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423688B1

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