Water → HCID 67899259, compound

Participants

Reaction Conditions

Reaction Steps

15.9 g (17.9 mmol ) of benzhydryl 7-phenylacetamido-3-(triphenylphosphonio)methyl-3-cephem-4-carboxylate iodide (Example 7) are taken in 100 ml of methylene chloride and 17.56 g (250.6 mmol) of cyclopropanecarboxaldehyde in a 250 ml three-necked flask. The mixture is cooled to 0° C. and 100 ml of water are added. 16.3 ml of 1N NaOH are then added dropwise in the course of 4 hours, the pH being kept constant at 8.6. The reaction solution is diluted with methylene chloride and the organic phase is separated off, washed once with water and then dried over sodium sulphate. After the drying agent has been removed, a further 13 ml (233 mmol) of cyclopropanecarboxaldehyde are added to the methylene chloride solution and the mixture is stirred overnight. The reaction solution is then concentrated to dryness, the residue is again dissolved in a little methylene chloride and the mixture is introduced onto a column filled with 500 ml of silica gel (0.04-0.063 mm). 400 ml fractions are collected and all the fractions are investigated for the cis-isomer compound by means of analytical HPLC.

Provenance & Evidence