Trimethylamine → HCID 88701876, compound

Participants

Reaction Steps

To a stirred suspension of 7-amino-3-acetoxymethylceph-3-em-4-carboxylic acid toluene-p-sulphonate dihydrate (19.2 g., 40 mmole) in anhydrous THF (500 ml.) under nitrogen in a 1 liter flask was added triethylamine (dried over potassium, 27.76 ml., 200 mmole) then trimethylchlorosilane (20.18 ml., 17.36 g., 160 mmole) while maintaining the temperature at 20° with a cooling bath. After 30 minutes a further 10% of triethylamine and 10% of trimethylchlorosilane were added and the reaction mixture was allowed to stir for a further 2.5 hours. To the mixture was then added acetic formic mixed anhydride (7.04 g., 80 mmole) with cooling in an ice bath. A further 10% trimethylamine, 10% trimethylchlorosilane and 20% acetic formic mixed anhydride, and then yet a further 10% of all three reagents were added to achieve complete disappearance of starting material on t.l.c. Water was then added, the suspension was filtered on a sintered glass disc and the solid dried to give 3-acetoxymethyl-7-formylaminoceph-3-em-4-carboxylic acid.

Provenance & Evidence