Tributylvinyltin → HCID 14167864, compound

HRID 1608372Notes

Reaction equation

HRID 1608372 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[C:15](OS(C(F)(F)F)(=O)=O)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:44]([Sn](CCCC)(CCCC)CCCC)=[CH2:45].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN1CCCC1=O.[Cl-].[Zn+2].[Cl-]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:42](=[O:43])[N:13]3[C:14]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[O:27])=[C:15]([CH:44]=[CH2:45])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 521585Tris(furan-2-yl)phosphaneHCID 14167862HCID 14167862, compound

Product 1

HCID 14167864HCID 14167864, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 0.4645 g (0.00073 mole) of diphenylmethyl 7-phenylacetamido-3-trifluoromethylsulfonyloxy-3-cephem4-carboxylate, 0.279 g (0.00088 mole) of ethenyl tri-n-butylstannane, 0.200 g (0.00146 mole) of zinc chloride and 0.0068 g (0.000029 mole) of tri-(2-furyl)phosphine in 6 mL of dry 1-methyl-2-pyrrolidinone, under an Argon atmosphere, was degassed for 30 seconds. Then 0.0084 g (0 000014 mole) of palladium(0) bis(dibenzylidene acetone) was added all at once. The reaction mixture was stirred at room temperature for 1 hr. The reaction mix was then diluted with ethyl acetate and the organic solution washed with dilute ammonium chloride. The ethyl acetate was removed at reduced pressure and replaced with acetonitrile. The organic phase was washed with n-pentane and the acetonitrile removed at reduced pressure. The residue was crystallized from ethanol/methylene chloride yielding 0.320 g (85%) of diphenylmethyl 7-phenylacetamido-3-ethenyl-3-cephem-4-carboxylate. The nuclear magnetic resonance spectrum was consistent for the desired structure.

Workup

  1. customunder an Argon atmosphere, was degassed for 30 seconds
  2. additionThen 0.0084 g (0 000014 mole) of palladium(0) bis(dibenzylidene acetone) was added all at once
  3. additionThe reaction mix
  4. additionwas then diluted with ethyl acetate
  5. washthe organic solution washed with dilute ammonium chloride
  6. customThe ethyl acetate was removed at reduced pressure
  7. washThe organic phase was washed with n-pentane
  8. customthe acetonitrile removed at reduced pressure
  9. customThe residue was crystallized from ethanol/methylene chloride yielding 0.320 g (85%) of diphenylmethyl 7-phenylacetamido-3-ethenyl-3-cephem-4-carboxylate

Sources & evidence

ORD record
ord-6db2ec81b55544eab9539c03a973184d
Source dataset
uspto-grants-1989_09
Patent number
US04870168

Reaction notes

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