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

HRID 2374840

Reaktionsgleichung

Reaktionsgleichung von HRID 2374840
[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-f728bf8a555544368d5eac68a00fa0d3
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462630B2

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