Hydrochloric Acid → Diphenylmethyl 3-(2-acetylhydrazono)methyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate

Participants

Reaction Steps

In a procedure similar to that described in Example I-3, diphenylmethyl 3-formyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate (104 mg) and acetylhydrazine (30 mg) are left to react in a mixture of tetrahydrofuran (8 ml) and water (1.51 ml) in the presence of hydrochloric acid (2 equivalents) at room temperature overnight to give diphenylmethyl 3-(2-acetylhydrazono)methyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate (101 mg). m.p. 130-138° C. Yield: 88%. IR: νmaxNujol 3250, 1782, 1715, 1670, 1597, 1535 cm-1. UV: λmaxEtOH 327nm(ε=24000). NMR: δCDCl 3 (60MHz) 220s3H, 3.72ABq(39;18Hz)2H, 3.82s2H, 5.00d(5Hz)1H, 5.87dd (9;5Hz)1H, 6.77-7.58ml5H, 8.05s1H, 9.65s1H. [α]D23 -258° (c= 0.493,CHCl3).

Provenance & Evidence