Dimethylformamide → Diphenylmethyl 3-azidomethyl-7-(imidazol-2-yl)aminoceph-3-em-4-carboxylate hydrochloride

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Reaction Steps

A mixture of diphenylmethyl 7-amino-3-azidomethylceph-3-em-4-carboxylate (1.2 g.), 2-fluoroimidazole hydrochloride (367 mg.) and acetonitrile (4 ml.) was stirred at 85°. When a complete solution was achieved DMF (1 ml.) was added. After 2 hours the solvent was evaporated and the residue, after drying overnight, was purified by chromatography on fine mesh silica (ratio 40:1 w/w) at 0° using methylene chloride/MeOH/HOAc 100:0:0 to 92:4:4 v/v/v as eluant. The oil obtained was dissolved in the minimum of methylene chloride and precipitated with ether. After drying there was obtained diphenylmethyl 3-azidomethyl-7-(imidazol-2-yl)aminoceph-3-em-4-carboxylate hydrochloride (38%) as a white powder having the following n.m.r. in solent A: 3.65 (d, 1H); 3.8 (d, 1H); 3.95 (d, 1H); 4.3 (d, 1H); 5.3 (d, 1H); 5.85 (d, 1H); 6.9 (s, 2H); 7.0 (s, 1H); 7.5-7.7 (m, 10H).

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