Reaction #5644

ord-d423bb0af2d64620abf46421b8a2f7ef

Reaction equation

O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OC(c3ccccc3)c3ccccc3)=C(OS(=O)(=O)c3ccc(Br)cc3)CS[C@H]12

product

Diphenylmethyl 7-Phenoxyacetamido-3-[(4-bromophenylsulfonyl)oxy]-3-cephem-4-carboxylate

$C/C=[CH]\[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC$

Z-1-propenyl-tri-n-butylstannane

4-bromobenzenesulfonyl chloride

→

$C/C=C\C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1$

title compound

$C/C=C\C1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C(NC(=O)COc3ccccc3)[C@H]2SC1$

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

Reactants

product

Diphenylmethyl 7-Phenoxyacetamido-3-[(4-bromophenylsulfonyl)oxy]-3-cephem-4-carboxylate

$C/C=[CH]\[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC$

Z-1-propenyl-tri-n-butylstannane

4-bromobenzenesulfonyl chloride

Reagents

palladium (II) acetate

Solvents

1-methyl-2-pyrrolidinone

Conditions

Detailed conditions

See reaction.notes.procedure_details.

Workup

1
workup.ADDITIONThe reaction mix

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%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05245027uspto-grants-1993_09