2,6-Lutidine → methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

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Reaktionsgleichung

N1C(C)=CC=CC=1C.P(Cl)(Cl)(Cl)=O.[CH:14]([NH:16][C@@H:17]1[C@@H:20]([CH2:21][CH:22]=[CH2:23])[N:19]([C:24](=[C:29]([CH3:31])[CH3:30])[C:25]([O:27][CH3:28])=[O:26])[C:18]1=[O:32])=O.C(OCC)(=O)C>ClCCl.[Cl-].[Na+].O>[N+:16]([C@@H:17]1[C@@H:20]([CH2:21][CH:22]=[CH2:23])[N:19]([C:24](=[C:29]([CH3:31])[CH3:30])[C:25]([O:27][CH3:28])=[O:26])[C:18]1=[O:32])#[C-:14]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

2,6-Lutidine (3.82 ml) and phosphorus oxychloride (1.37 ml) were added to a solution of methyl 2-[(3R,4R)-3-formamido-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (970 mg) in dichloromethane (10 ml) at 0° C., and the mixture was stirred for three hours at 0° C. Then, the reaction mixture was poured into a mixture of ethyl acetate (100 ml) and brine (50 ml). The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The oily residue was chromategraphed on silica gel (15 g) eluting with a mixture of hexane and ethyl acetate (10:1-3:1) to give methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (766 mg) as an oil.

Aufarbeitung

washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
washeluting with a mixture of hexane and ethyl acetate (10:1-3:1)

Quellen und Nachweise

ORD-Eintrag: ord-0bde6fed36004a0ebeec66ff7d3f7462
Quelldatensatz: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04383945

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