Реакция #65628

Уравнение реакции

Z-1-propenyl tri-n-butylstannane

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

→

title compound

Выход 92.9%

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

Выход 92.9%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGto stir for 10 minutes
2. 2
   Промывкаwashed with water (1×10 mL)
3. 3
   СушкаThe organic fraction was dried over magnesium sulfate
4. 4
   Фильтрацияpurified by flash filtration through a pad of silica gel (W. R. Grace, 951W) first with dichloromethane (50 mL)
5. 5
   Другоеto remove the residual stannane
6. 6
   Концентрированиеwith 10% ethyl acetate in dichloromethane (50 mL) which upon concentration

Методика

A solution of palladium (II) acetate (3.6 mg, 0.016 mmole, 0.1 eq.) in dichloromethane (2 mL) was treated with Z-1-propenyl tri-n-butylstannane (66.2 mg, 0.2 mmole, 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 mmole, 1.0 eq.) in one portion and the reaction mixture was allowed to stir for 10 minutes. The reaction mixture was diluted with additional dichloromethane and washed with water (1×10 mL). The organic fraction was dried over magnesium sulfate and 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 (50 mL) which upon concentration furnished 80.4 mg (89%) of the title compound as a pale yellow solid. The product was then recrystallized from isopropyl alcohol to afford 62.3 mg (69%) of a white solid, mp. 103°-104° C.

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