Synthesis of amino acid and 4,5-dihydro-6H-1,3-thiazine derivatives for the preparation of cephalosporin compounds.

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Abstract

Several β-hydroxy-α-halogeno-α-amino acid derivatives (3-5) were prepared from tert-butyl N-benzylideneglycinate (1) and α-haloketones or an α-haloaldehyde for utilization in the synthesis of 4, 5-dihydro-6H-1, 3-thiazine derivatives (7 and 12). An alternative thiazine synthesis starting from tert-butyl glycinate (13) was found to proceed stereoselectively, giving rise to 12a. The two thiazine derivatives 7 and 12a were converted into cephalosporin derivatives (10 and 17, respectively) by reaction with azidoacetyl chloride. The 7-azido-3-methylcephem derivative (17) was further led to 7-aminodeacetoxycephalosporanic acid (7-ADCA, 22).

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