Water → HCID 15170714, Verbindung

HRID 486879

Reaktionsgleichung

Reaktionsgleichung von HRID 486879
[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)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[SH:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][S:8][C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 962WaterHCID 6456Trityl chlorideHCID 656604Bucillamine

Produkt 1

HCID 15170714HCID 15170714, VerbindungAusbeute 60,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of N-(2-mercapto-2-methylpropionyl)-L-cysteine (11.2 g) in dimethylformamide(50 ml), trityl chloride(16.7 g) was added slowly. The reaction mixture was stirred for 2 hours at room temperature, poured into water and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 14.2 g(60%) of the titled compound.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue was purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-77763c7cf282419bbad470935c97cf60
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292926

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