2,6-Lutidine → N-t-butyldimethylsilyloxycarbonylvaline methyl ester

HRID 1904445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1904445
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH:13]([CH3:15])[CH3:14])[NH:5][C:6]([O:8]C(C)(C)C)=[O:7].N1C(C)=CC=CC=1C.[Si:25](OS(C(F)(F)F)(=O)=O)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[Cl-].[NH4+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH:13]([CH3:14])[CH3:15])[NH:5][C:6]([O:8][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[O:7]

Komponenten

6

Edukt 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 11031717N-(tert-Butoxycarbonyl)-L-valine methyl ester

Produkt 1

HCID 13934325N-t-butyldimethylsilyloxycarbonylvaline methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a methylene chloride solution (1.0 ml) of N-t-butoxycarbonyl-L-valine methyl ester (115.5 mg, 0.5 mmol) and 2,6-lutidine (0.116 ml, 1.0 mmol) was added dropwise t-butyldimethylsilyltrifluoromethane sulfonate (0.172 ml, 0.75 mmol) at room temperature in a nitrogen atmosphere. After the mixture was stirred for 15 minutes, a saturated aqueous solution of ammonium chloride (2 ml) was added to quench the reaction and extraction with ether was conducted. The organic layer was dried over anhydrous magnesium sulfate and filtered. By distilling off the solvent under vacuum, the titled compound was obtained in an amount of 153.2 mg.

Aufarbeitung

  1. customto quench
  2. customthe reaction and extraction with ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationBy distilling off the solvent under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b943ef89acb54ada8861d8394caf3533
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04837349

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