Methanol → Penicillamine methyl ester

HRID 719667

Reaktionsgleichung

Reaktionsgleichung von HRID 719667
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].S(Cl)(Cl)=O.[CH3:14]O>>[NH2:1][C@@H:2]([C:3]([SH:6])([CH3:5])[CH3:4])[C:7]([O:9][CH3:14])=[O:8]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 92863L-Penicillamine

Produkt 1

HCID 153004Penicillamine methyl esterAusbeute 100 %

Versuchsvorschrift

To a methanol (18 mL, 1.14 M) solution containing L-penicillamine (3.0 g, 20.11 mmol, 1.0 eq) was added thionyl chloride (1.5 mL, 20.7 mmol, 1.03 eq). The resulting mixture was heated to reflux for 18 hr and the solvent removed in vacuo. The resulting clear semi-solid was used in the next step without further purification. Isolated 3.28 g (20.1 mmol, 100% yield).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 18 hr
  3. customthe solvent removed in vacuo
  4. customThe resulting clear semi-solid was used in the next step without further purification
  5. customIsolated 3.28 g (20.1 mmol, 100% yield)

Quellen und Nachweise

ORD-Eintrag
ord-bd5e1b8e45af41ca92ca3e05f5afe5be
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132443B2

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