O-Phenylenediamine → HCID 70508553, compound

Participants

Reaction Steps

To a solution of diphenylmethyl 3-acetoxymethyl-7-dibromomethyleneaminoceph-3-em-4-carboxylate (0.608 g., 1 mmole) in THF stirred under nitrogen at ambient temperature was added orthophenylenediamine (0.216 g., 2 mmole) in THF and the reaction was allowed to continue stirring for 4 hours. The solution was then evaporated to dryness and the residue was dissolved in CH2Cl2 containing a little methanol. This solution was chromatographed on silica gel (50 g.) at -40° using CH2Cl2 /MeOH 85:15 v/v as eluant to give diphenylmethyl 3-acetoxymethyl-7-(benzimidazol-2-yl)aminoceph-3-em-4-carboxylate (0.39 g.). The product had the following n.m.r. spectrum in CDCl3 : 1.92(s,3H); 3.25(m,2H); 4.57(d,1H); 4.97(d,1H); 5.15(d,1H); 5.90(d,1H); 6.85(s,1H); 3.25(m,10H).

Provenance & Evidence