Reaktion #5641

Reaktionsgleichung

vinyl tri-n-butylstannane

diphenylmethyl 7-phenoxyacetamido-3-[(fluorosulfonyl) oxy]-3-cephem-4-carboxylate

→

title compound

Ausbeute 88.8%

Diphenylmethyl 7-Phenoxyacetamido-3-vinyl-3-cephem-4-carboxylate

Ausbeute 88.8%

Lösungsmittel

ethyl acetate

1-methyl-2-pyrrolidinone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir for 10 minutes
2. 2
   Waschenwashed with 3×20 mL of water
3. 3
   TrocknenThe organic fraction was dried over magnesium sulfate
4. 4
   Einengenthen concentrated
5. 5
   FiltrationThe crude brown residue was purified by flash filtration through a pad of silica gel (W. R. Grace, 951W) first with dichloromethane (50 mL)
6. 6
   Sonstigeto remove the residual stannane
7. 7
   Einengenwith 10% ethyl acetate in dichloromethane (75 mL), which upon concentration

Vorschrift

A solution of palladium (II) acetate (3.6 mg, 0.016 mmol, 0.1 eq.) in 1-methyl-2-pyrrolidinone (2 mL) was treated with vinyl tri-n-butylstannane (58.4 mL, 0.2 mmol, 1.2 eq.) under an inert atmosphere and allowed to stir for 3 minutes. The resulting dark suspension was then treated with diphenylmethyl 7-phenoxyacetamido-3-[(fluorosulfonyl) oxy]-3-cephem-4-carboxylate (100.0 mg, 0.16 mmol, 1.0 eq.) in one portion and the reaction mixture was allowed to stir for 10 minutes. The reaction mixture was diluted with ethyl acetate and washed with 3×20 mL of water. The organic fraction was dried over magnesium sulfate then concentrated. The crude brown residue was purified by flash filtration through a pad of silica gel (W. R. Grace, 951W) first with dichloromethane (50 mL) to remove the residual stannane and then with 10% ethyl acetate in dichloromethane (75 mL), which upon concentration furnished 74.8 mg (85%) of the title compound as a white solid.

Quelle