반응 #5642

반응 방정식

Z-1-propenyl tri-n-butylstannane

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

→

title compound

수율 92.9%

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

수율 92.9%

용매

dichloromethane

dichloromethane

반응 조건

후처리

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

실험 절차

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.

출처