1H-Isoindole-1,3(2H)-dione, 2-(trimethylsilyl)- → HCID 21161747, compound

Participants

Reaction Steps

B.A solution of 1.1 g (3 mmoles) of 6-phthalimidopenicillanic acid-R-sulphoxide in 20 ml of dimethylacetamide was treated with 4 g (18 mmoles) of N-trimethylsilylphthalimide at 100°C. After 4 hours the mixture (containing 1-(1-trimethylsilyloxycarbonyl-2-methylprop-2-enyl)-3-phthalimido-4-phthalimidothio-azetidin-2-one) was concentrated, the residue was dissolved in 30 ml of dichloromethane and the solution was filtered. The filtrate was purified by chromatography on a silica gel column impregnated with 1% acetic acid, using a 4:1 (v/v) mixture of toluene and acetone containing 0.5% acetic acid as an eluent. There were obtained 100 mg of 7-phthalimido-Δ3 -desacetoxycephalosporanic acid and 210 mg of 1-(1-carboxy-2-methylprop-2-enyl)-3-phthalimido-4-phthalimidothio-azetidin-2-one contaminated with dimethylacetamide.

Provenance & Evidence