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

HRID 37349

Reaktionsgleichung

Reaktionsgleichung von HRID 37349
[CH:1]([Sn](CCCC)(CCCC)CCCC)=[CH2:2].[O:16]([CH2:23][C:24]([NH:26][CH:27]1[C:55](=[O:56])[N:29]2[C:30]([C:39]([O:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])=[C:31](OS(F)(=O)=O)[CH2:32][S:33][C@H:28]12)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN1CCCC1=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:16]([CH2:23][C:24]([NH:26][CH:27]1[C:55](=[O:56])[N:29]2[C:30]([C:39]([O:41][CH:42]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])=[C:31]([CH:1]=[CH2:2])[CH2:32][S:33][C@H:28]12)=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

6

Edukt 2

HCID 81998TributylvinyltinHCID 88424184Diphenylmethyl 7-Phenoxyacetamido-3-[(fluorosulfonyl)oxy]-3-cephem-4-carboxylate

Produkt 1

HCID 14608937Diphenylmethyl 7-Phenoxyacetamido-3-vinyl-3-cephem-4-carboxylateAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. stirringto stir for 10 minutes
  2. washwashed with 3×20 mL of water
  3. dry with materialThe organic fraction was dried over magnesium sulfate
  4. concentrationthen concentrated
  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. customto remove the residual stannane
  7. concentrationwith 10% ethyl acetate in dichloromethane (75 mL), which upon concentration

Quellen und Nachweise

ORD-Eintrag
ord-d1f2a9fd35f84e6e8a411800ef17dff0
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420269

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