4-Nitrobenzyl 2-diazo-4-((2R,3S)-3-((R)-1-hydroxyethyl)-4-oxoazetidin-2-YL)-3-oxobutanoate → (4-Nitrophenyl)methyl (5R,6S)-6-((1R)-1-hydroxyethyl)-3,7-dioxo-1-azabicyclo(3.2.0)heptane-2-carboxylate

HRID 64811

Reaktionsgleichung

[OH:1][C@@H:2]([C@@H:4]1[C@@H:7]([CH2:8][C:9](=[O:26])[C:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[O:14])=[N+]=[N-])[NH:6][C:5]1=[O:27])[CH3:3]>C1C=CC=CC=1.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[OH:1][C@@H:2]([C@H:4]1[C:5](=[O:27])[N:6]2[C@@H:7]1[CH2:8][C:9](=[O:26])[CH:10]2[C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=1)=[O:14])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 78 °C

Versuchsvorschrift

A suspension of (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one (56.4 mg, 0.15 mmol) and rhodium (II) acetate (0.1 mg) in dry benzene (3 ml) is deoxygenated by bubbling through nitrogen for 10 minutes. The mixture is then heated to 78° C. for 1 hour. During heating the solid starting material gradually goes into solution. The mixture is then cooled, filtered to remove the catalyst, and the filtrate is concentrated in vacuo to yield (5R,6S) p-nitrobenzyl 6-[(R)-1-hydroxyethyl]-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate, 51 mg. (98%) as a colorless oil which slowly crystallized at room temperature (22° C.).

Aufarbeitung

customis deoxygenated
customby bubbling through nitrogen for 10 minutes
temperatureDuring heating the solid
temperatureThe mixture is then cooled
filtrationfiltered
customto remove the catalyst
concentrationthe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-ca3e005acf88490a8935cb5657f4148f
Quelldatensatz: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04610820

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