Benzaldehyde → Benzhydryl 7-Benzylideneamino-3-triphenylphosphoniomethyl-3-cephem-4-carboxylate chloride

Participants

Reaction Steps

To a suspension of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride (II hydrochloride) (200 g, 0.44 mole) in CH2Cl2 (940 ml) was added 1N NaOH (440 ml) at room temperature. The mixture was shaken for 10 minutes and the organic layer was separated. To the organic layer were added MgSO4 (75 g) and benzaldehyde (51 g, 0.48 mole) and the mixture was allowed to stand for 3 hours. The reaction mixture was filtered and the insolubles were washed with CH2Cl2 (200 ml). To the combined filtrate and washings was added triphenylphosphine (126 g, 0.48 mole). The mixture was concentrated to about 400 ml and allowed to stand for 4 days. The resulting viscous oil was diluted with ethyl acetate (1 L) and triturated to separate the title compound XV a pale yellow crystalline powder which was collected by filtration and dried in vacuo. Yield 322 g (96%). M.p. 185°-190° C. (dec.).

Provenance & Evidence