Reaktion #460533

Reaktionsgleichung

water

diphenylmethyl 7-t-butoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thio]-3-cephem-4-carboxylate

triphenyl phosphine

Z-1-propenyltributyl stannane

→

title product

Ausbeute 139.8%

Diphenylmethyl 7-t-Butoxycarbonyl-3-(Z)-1-propenyl-3-cephem-4-carboxylate

Ausbeute 139.8%

Lösungsmittel

ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed under argon atmosphere for 20 h
2. 2
   SonstigeThe organic phase was separated
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated
5. 5
   workup.DISSOLUTIONThe crude product dissolved in acetonitrile
6. 6
   Waschenthe acetonitrile solution was washed three times with equal volumes of pentane

Vorschrift

A mixture of diphenylmethyl 7-t-butoxycarbonyl-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)thio]-3-cephem-4-carboxylate (IId, 0.125 g, 0.000215 mole), bis(dibenzylideneacetone)palladium (0.0062 g, 0.00001075 mole), triphenyl phosphine (0.0084 g, 0.000032 mole), zinc chloride (0.0586 g, 0.00043 mole) and Z-1-propenyltributyl stannane (0.071 g, 0.000215 mole) in dry tetrahydrofuran (2 mL) was refluxed under argon atmosphere for 20 h. After no further conversion of starting compound IId took place, water and ethyl acetate were added. The organic phase was separated, dried and concentrated. The crude product dissolved in acetonitrile and the acetonitrile solution was washed three times with equal volumes of pentane. Flash chromatography with 20% ethyl acetate in hexane gave the title product (0.022 g, 20%) as a foam. Also recovered was 0.0435g (34.8%) of starting compound IId.

Quelle