Hydrochloric Acid → HCID 12876158, Verbindung

HRID 127294

Reaktionsgleichung

Reaktionsgleichung von HRID 127294
[SH:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][SH:8])=[O:4].[C:14](Cl)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16].Cl>[OH-].[Na+]>[C:14]([S:8][CH2:7][C@@H:6]([C:9]([OH:11])=[O:10])[NH:5][C:3](=[O:4])[C:2]([SH:1])([CH3:13])[CH3:12])(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 62493Pivaloyl chlorideHCID 656604Bucillamine

Produkt 1

HCID 12876158HCID 12876158, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-(2-Mercapto-2-methylpropanoyl)-L-cysteine (11.2 g, 0.05 mol) is dissolved in N sodium hydroxide (50 ml) and then pivaloyl chloride (6.6 g, 0.055 mol) and N sodium hydroxide (60 ml) are added dropwise while stirring under a nitrogen atmosphere at 0° C. After the addition, the mixture is stirred for 1 hour at room temperature and acidified with 6 N hydrochloric acid. The produced oil is extracted with ethyl acetate. The organic layer is washed with water, dried and concentrated to dryness to yield 11.5 g (75.0%) S-pivaloyl-N-(2-mercapto-2-methylpropanoyl)-L-cysteine.

Aufarbeitung

  1. additionAfter the addition
  2. stirringthe mixture is stirred for 1 hour at room temperature
  3. extractionThe produced oil is extracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-9f70f753115c4457a6e4c7a2c15df00b
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04255446

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