Levodopa → Melevodopa

HRID 1024552

Reaktionsgleichung

Reaktionsgleichung von HRID 1024552
[C:1](Cl)(=O)C.[CH:5]1[C:10]([CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=[O:14])=[CH:9][C:8]([OH:17])=[C:7]([OH:18])[CH:6]=1>CO>[CH3:1][O:14][C:13]([C@@H:12]([NH2:16])[CH2:11][C:10]1[CH:5]=[CH:6][C:7]([OH:18])=[C:8]([OH:17])[CH:9]=1)=[O:15]

Komponenten

4

Edukt 2

HCID 6047LevodopaHCID 6367Acetyl chloride

Produkt 1

HCID 23497MelevodopaAusbeute 117,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
15 °C

Versuchsvorschrift

A 3-Liter three-necked round-bottom flask equipped with a cooling bath, a thermometer and a condenser was charged with 1.5 Liters methanol, and acetyl chloride (119 ml, 1.2 mol) was carefully added thereto at 0° C. The cooling bath was replaced with a heating mantle and the mixture was heated to 15° C. 60 grams (0.3 mol) of L-3-(3,4-dihydroxy-phenyl)alanine was then added and the reaction mixture was refluxed for 3 hours and thereafter concentrated under reduced pressure at 60° C. to afford 74.3 grams (100% yield) of Compound 2 (see, Scheme 1). The product structure was confirmed by 1H-NMR.

Aufarbeitung

  1. customA 3-Liter three-necked round-bottom flask equipped with a cooling bath
  2. additionwas carefully added
  3. customat 0° C
  4. temperaturethe reaction mixture was refluxed for 3 hours
  5. concentrationconcentrated under reduced pressure at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-556db68ae9ce4eb4bbd34788f1379f94
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722923B2

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