Water → 2-Benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyric acid

HRID 1088095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088095
[CH2:1]([O:8][C:9]([CH2:11][O:12][N:13]=[C:14]([C:22](=[O:24])[CH3:23])[C:15]([O:17]C(C)(C)C)=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.[BrH:34].[NH+]1C=CC=CC=1.O>O1CCCC1>[CH2:1]([O:8][C:9]([CH2:11][O:12][N:13]=[C:14]([C:22](=[O:24])[CH2:23][Br:34])[C:15]([OH:17])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 21226041Pyridinium hydrobromideHCID 53811665Tert-butyl 2-benzyloxycarbonylmethoxyimino-3-oxobutyrate

Produkt 1

HCID 540321592-Benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-benzyloxycarbonylmethoxyimino-3-oxobutyrate (2.0 g) in dry tetrahydrofuran (20 ml) were added boron trifluoride diethyl etherate (3.0 ml) and pyridinium hydrobromide perbromide (3.0 g) at ambient temperature, followed by stirring for 6 hours. The reaction mixture was poured into water (50 ml) and then extracted twice with ethyl acetate (70 ml). The combined extracts were washed with 10% hydrochloric acid and then a saturated aqueous sodium chloride, followed by drying over magnesium sulfate. Removal of the solvent gave 2-benzyloxycarbonylmethoxyimino-4-bromo-3-oxobutyric acid (2.0 g).

Aufarbeitung

  1. extractionextracted twice with ethyl acetate (70 ml)
  2. washThe combined extracts were washed with 10% hydrochloric acid
  3. dry with materialby drying over magnesium sulfate
  4. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-913a0e8c25474112ae446635ae04eb47
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04960889

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