(Z)-Tri-n-butyl(1-propenyl)tin → Diphenylmethyl 7-Phenoxyacetamido-3-(Z-1-propenyl)-3-cephem-4carboxylate

HRID 37350

Reaction equation

HRID 37350 reaction equation
[CH:1](/[Sn](CCCC)(CCCC)CCCC)=[CH:2]/[CH3:3].[O:17]([CH2:24][C:25]([NH:27][CH:28]1[C:56](=[O:57])[N:30]2[C:31]([C:40]([O:42][CH:43]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])=[C:32](OS(F)(=O)=O)[CH2:33][S:34][C@H:29]12)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:17]([CH2:24][C:25]([NH:27][CH:28]1[C:56](=[O:57])[N:30]2[C:31]([C:40]([O:42][CH:43]([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])=[C:32](/[CH:1]=[CH:2]\[CH3:3])[CH2:33][S:34][C@H:29]12)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 10914524(Z)-Tri-n-butyl(1-propenyl)tinHCID 88424184Diphenylmethyl 7-Phenoxyacetamido-3-[(fluorosulfonyl)oxy]-3-cephem-4-carboxylate

Product 1

HCID 14608940Diphenylmethyl 7-Phenoxyacetamido-3-(Z-1-propenyl)-3-cephem-4carboxylateYield 92.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  1. stirringto stir for 10 minutes
  2. washwashed with water (1×10 mL)
  3. dry with materialThe organic fraction was dried over magnesium sulfate
  4. filtrationpurified by flash filtration through a pad of silica gel (W. R. Grace, 951W) first with dichloromethane (50 mL)
  5. customto remove the residual stannane
  6. concentrationwith 10% ethyl acetate in dichloromethane (50 mL) which upon concentration

Sources & evidence

ORD record
ord-512fd01efe9d4d2bbe59666e4c073c20
Source dataset
uspto-grants-1995_05
Patent number
US05420269

Linked notes

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