Formaldehyde → HCID 13035130, compound

Participants

Reaction Steps

A solution of [4-diphenylmethoxycarbonyl-7β-(2-thienylacetamido)ceph-3-em-3-ylmethyly] triphenylphosphonium iodide (430 mg.), RF 0.0, in methylene chloride (10 ml.) was shaken with 5%-sodium bicarbonate solution (10 ml.) for five minutes. The separated organic layer was treated with 40%-formaldehyde solution (2 ml.) and 5% aqueous sodium bicarbonate solution (5 ml.) and the mixture stirred vigorously at room temperature until the chromophore of the starting material at 388 nm. had disappeared (ca. 30 minutes). The organic layer was separated and washed with 0.5N-hydrochloric acid and water, then dried and evaporated in vacuo. The residue was crystallised from methanol to give diphenylmethyl 7β-(2-thienylacetamido)-3-vinylceph-3-em-4-carboxylate (90 mg. 36%), RF 0.5, as needles, λmax. 296 nm. (ε 13,200), identified by infrared spectroscopy with material described previously.

Provenance & Evidence