Efficient procedure for c '- 3 substitution and c - 7 n-acylation of 7-aminocepha-losporanic acid (7-aca): Synthesis of cefazolin antibiotic and related compounds |
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Authors: | Alberto Palomo-coll Antonio L. Palomo Coll Claudio Palomo Nicolau |
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Affiliation: | Departamento Científico, GEMA S.A., Beethoven 15, 08021 BarcelonaSpain;Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad del País Vasco, Alza, San SebastiánSpain |
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Abstract: | A new preparative method for the C'-3 substitution of 7-aminocepha-losporanic acid (7-ACA), is described. The key feature of our method is based on the protection of the anino group as a Schiff base instead of the usual procedure based on the acylation of the amino group. The relative incapacity of 7-ACA derivatives to produce organic solutions with usual tertiary bases is easily overcome with bicyclic amidines. Catalytic amounts of these bases and N-trimethylsilyl-2-oxazolidinone are used to obtain the silylated products. Activation of sensitive tetrazolylacetic acid by means of N,N-dimethylchloro-sulfitemethaniminium chloride (SOCl2-DMF) and preparation of cefazolin antibiotic under anhydrous conditions is also described. |
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