p-Bromobenzenesulfonyl chloride → Diphenylmethyl 7-Phenoxyacetamido-3-(Z-1-propenyl)-3-cephem-4carboxylate

HRID 37352

Reaction equation

HRID 37352 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:46](=[O:47])[N:14]2[C:15]([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])=[C:16](OS(C3C=CC(Br)=CC=3)(=O)=O)[CH2:17][S:18][C@H:13]12)=[O:10])C1C=CC=CC=1.[CH:48](/[Sn](CCCC)(CCCC)CCCC)=[CH:49]/[CH3:50].Br[C:65]1[CH:70]=[CH:69][C:68](S(Cl)(=O)=O)=[CH:67][CH:66]=1>CN1CCCC1=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:46](=[O:47])[N:14]2[C:15]([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])=[C:16](/[CH:48]=[CH:49]\[CH3:50])[CH2:17][S:18][C@H:13]12)=[O:10])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

6

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 10914524(Z)-Tri-n-butyl(1-propenyl)tinHCID 88424480Diphenylmethyl 7-Phenoxyacetamido-3-[(4-bromophenylsulfonyl)oxy]-3-cephem-4-carboxylate

Product 1

HCID 14608940Diphenylmethyl 7-Phenoxyacetamido-3-(Z-1-propenyl)-3-cephem-4carboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 0.184 g (0.00025 mole) of the product of Procedure 6, 0.103 g (0.0003215 mole) of Z-1-propenyl-tri-n-butylstannane and 0.0064 g (0.000025 mole) of 4-bromobenzenesulfonyl chloride in 2.5 mL of 1-methyl-2-pyrrolidinone, under a nitrogen atmosphere, at room temperature was added 0.006 g (0.000025 mole) of palladium (II) acetate. The reaction mix was stirred at room temperature for 20 hours. High pressure liquid chromatography (HPLC) analysis of the reaction mixture showed a peak for the title compound with retention time identical to an authentic sample of the title compound. The HPLC area percent for this peak was 21.2%

Workup

  1. additionThe reaction mix

Sources & evidence

ORD record
ord-f86fc6d7f8e94672a1ee048686633371
Source dataset
uspto-grants-1995_05
Patent number
US05420269

Linked notes

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