Imidazole → 2-{[(benzyloxy)carbonyl]amino}-3-{[t-butyl(dimethyl)silyl]oxy}propionic Acid

HRID 2236021

Reaktionsgleichung

Reaktionsgleichung von HRID 2236021
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:15]([OH:17])=[O:16])[CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:23]([Si:27]([CH3:30])([CH3:29])Cl)([CH3:26])([CH3:25])[CH3:24].O>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:13][O:14][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:30])[CH3:29])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 76007N-carbobenzoxy-serine

Produkt 1

HCID 4955662-{[(benzyloxy)carbonyl]amino}-3-{[t-butyl(dimethyl)silyl]oxy}propionic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.50 g (6.27 mmol) of N-[(benzyloxy)carbonyl]-(DL)-serine was dissolved in 10 ml of N,N-dimethylformamide. 885 mg (13.2 mmol) of imidazole and 1.98 g (13.2 mmol) of t-butyldimethylchlorosilane were added to the obtained solution at 0° C., and they were stirred overnight. Water was added to the reaction mixture and they were stirred for 10 minutes. After extracting with ethyl acetate 3 times followed by the drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain the title compound.

Aufarbeitung

  1. stirringwere stirred for 10 minutes
  2. extractionAfter extracting with ethyl acetate 3 times
  3. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-490deeec73db4de2beddd0bd11d5c5b5
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713957B2

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