N,O-bis(trimethylsilyl)acetamide → Diisopropyl Ether

Participants

Reaction Conditions

Reaction Steps

To a mixture of N,O-bis(trimethylsilyl)acetamide (2.3 ml, 9 mmoles) and crystalline diphenylmethyl 7-amino-3-[3-chloro-1-(Z)-propen-1-yl]-3-cephem-4-carboxylate hydrochloride (XVIII) (1.338 g, 2.8 mmoles) (from Preparation No. 12) in methylene chloride (10 ml) was added 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(Z)-ethoxyiminoacetyl chloride hydrochloride (800 mg, 2.95 mmoles) portionwise, with stirring, at -10° C. and the mixture was allowed to stand at 0° C. for 2 hours. The mixture was diluted with ethyl acetate (200 ml), washed with water and evaporated under reduced pressure. Trituration of the residue with isopropyl ether afforded the title product VIII-2 as an amorphous powder. Yield 1.70 g (95%). Mp. >150° C. (dec.).

Provenance & Evidence