Preparation and properties of 5-phenylphenoxymethylpenicillin.

@article{Vanderhaeghe1975PreparationAP,
  title={Preparation and properties of 5-phenylphenoxymethylpenicillin.},
  author={Hubert Vanderhaeghe and Jozef Thomis},
  journal={Journal of medicinal chemistry},
  year={1975},
  volume={18 5},
  pages={
          486-90
        }
}
Cycloaddition of azidoacetyl chloride to benzyl D-5,5-dimethyl-5-phenyl-2-thiazoline-4-carboxylate (1a) gave 5-phenyl-6alpha-azidopenicillanate (2a). By catalytic reduction of 2a and reaction with phenoxyacetyl chloride, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester (4a) was obtained. Oxidation of 4a gave the sulfoxide 6, which was isomerized in the presence of DBN. The sulfoxide 7 with the normal configuration could be isolated but deoxygenation of the sulfoxide was not successful… 
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