L-(+)-Cysteine → 2-Methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester

HRID 1503165

Reaktionsgleichung

Reaktionsgleichung von HRID 1503165
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[C:8]([O:13][CH2:14][CH3:15])(=[O:12])[C:9]([CH3:11])=O>O.C(O)C>[CH3:15][CH2:14][O:13][C:8]([C:9]1([CH3:11])[NH:1][CH:2]([C:5]([OH:7])=[O:6])[CH2:3][S:4]1)=[O:12]

Komponenten

5

Edukt 2

HCID 5862L-(+)-CysteineHCID 12041Ethyl pyruvate

Produkt 1

HCID 866809292-Methylthiazolidine-2,4-dicarboxylic acid 2-ethyl esterAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, L-cysteine (10 g) was dissolved in pure water (150 ml), and ethyl pyruvate (19.7 ml) dissolved in ethanol (10 ml) at room temperature was gradually added to the solution. The mixture was stirred overnight at room temperature, and concentrated under reduced pressure. The obtained solid was dissolved in pure water, and the solution was extracted with chloroform. The extract was dried over magnesium sulfate, and concentrated under reduced pressure to give an oil. The oil was recrystallized from chloroform/hexane to give 2-methylthiazolidine-2,4-dicarboxylic acid 2-ethyl ester (diastereomer mixture) (12.7 g, yield 70%).

Aufarbeitung

  1. additionwas gradually added to the solution
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe obtained solid was dissolved in pure water
  4. extractionthe solution was extracted with chloroform
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil
  8. customThe oil was recrystallized from chloroform/hexane

Quellen und Nachweise

ORD-Eintrag
ord-68684edfb80145f98519751caedce913
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212154B2

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