Acetic-formic anhydride → (6R,7R)-2,2-dimethyl-7-formamido-1-aza-3-oxabicyclo[4.2.0]octan-8-one
Reaktionsgleichung
[NH2:1][C@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[CH2:4][CH2:5][O:6][C:7]2([CH3:12])[CH3:11].[CH:13](OC(=O)C)=[O:14]>N1C=CC=CC=1>[CH3:11][C:7]1([CH3:12])[O:6][CH2:5][CH2:4][C@H:3]2[N:8]1[C:9](=[O:10])[C@@H:2]2[NH:1][CH:13]=[O:14]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of (6R,7R)-7-amino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one (300 mg) were added pyridine (0.25 ml) and freshly prepared acetic formic anhydride (0.38 ml) at 0° C. After stirring for 45 minutes at 0° C., the reaction mixture was evaporated in vacuo. The residue was dissolved in xylene and the solution was evaporated in vacuo. The residue was chromatographed on silica gel (6 g) eluting with a mixture of methylene chloride and methanol (25:1-10:1) to give (6R,7R)-2,2-dimethyl-7-formamido-1-aza-3-oxabicyclo[4.2.0]octan-8-one (378 mg) as an oil.
Aufarbeitung
- customthe reaction mixture was evaporated in vacuo
- dissolutionThe residue was dissolved in xylene
- customthe solution was evaporated in vacuo
- customThe residue was chromatographed on silica gel (6 g)
- washeluting with a mixture of methylene chloride and methanol (25:1-10:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-9ae8ee3b890047c29388213843cd51dc
- Quelldatensatz
- uspto-grants-1985_09
- Patentnummer
- US04539152
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