Boron trifluoride etherate → Benzyl 4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate

HRID 425419

Reaktionsgleichung

Reaktionsgleichung von HRID 425419
B(F)(F)F.CCOCC.[C:10]([NH:20][CH:21]([C:23]([OH:25])=[O:24])[CH3:22])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].CO[CH:28](OC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(OCC)C>[CH3:22][CH:21]1[C:23](=[O:25])[O:24][CH:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:20]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 62375Benzaldehyde dimethyl acetalHCID 95657N-(Benzyloxycarbonyl)-DL-alanine

Produkt 1

HCID 53400837Benzyl 4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Boron trifluoride diethyl etherate (12.56 mL, 100 mmol) was added to a −78° C. solution of N-carbobenzoxy-dl-alanine (4.47 g, 20 mmol) and benzaldehyde dimethyl acetal (2.97 mL, 19.8 mmol) in diethyl ether (100 mL). After stirring at ambient temperature for 4 days, the reaction mixture was recooled to 0° C., quenched with saturated aqueous sodium bicarbonate and extracted with diethyl ether. The combined organic extracts were dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 5-45% ethyl acetate/hexane afforded benzyl 4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate.

Aufarbeitung

  1. customwas recooled to 0° C.
  2. customquenched with saturated aqueous sodium bicarbonate
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined organic extracts were dried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1c0a8ef29fcd4dfabbecaa38303f60b4
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106070B2

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