Ethanol → (S)-isoserine ethyl ester hydrochloride

HRID 1587981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587981
S(Cl)([Cl:3])=O.COC1C=CC(COC([NH:15][CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[OH:18])=O)=CC=1.[CH2:24](O)[CH3:25]>>[ClH:3].[CH2:24]([O:21][C:19](=[O:20])[C@@H:17]([OH:18])[CH2:16][NH2:15])[CH3:25]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 127738164-methoxybenzyloxycarbonyl-(S)-isoserine

Produkt 1

HCID 86746976(S)-isoserine ethyl ester hydrochloride

Versuchsvorschrift

At 0°-5°, add thionyl chloride (2.80 ml) dropwise to N-(4-methoxybenzyloxycarbonyl)-(S)-isoserine (5.0 g) in absolute ethanol (100 ml). Heat the mixture under reflux for 1 hour and stir for 20 hours at room temperature. Concentrate the reaction mixture in vacuo and pour the reaction mixture into diethyl ether (300 ml), and filter the solid. Wash the solid with diethyl ether and dry in vacuo to give the title compound, an amber oil, [α]D26 =-19.8° (MeOH).

Aufarbeitung

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 1 hour
  3. concentrationConcentrate the reaction mixture in vacuo
  4. additionpour the reaction mixture into diethyl ether (300 ml)
  5. filtrationfilter the solid
  6. washWash the solid with diethyl ether
  7. customdry in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-61d0b6dc72a04ba68549abe8b776d6d3
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05219886

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