N-bromobutanimide → HCID 54377372, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.26 g (2 mmoles) of 1-(1p-nitro-benzyloxycarbonyl-2-methylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothio-azetidin-2-one, 0.71 g (4 mmoles) of N-bromosuccinimide, 50 mg (0.3 mmole) of azoisobutyronitrile and 80 ml of 1,2-dichloroethane was heated in the dark under nitrogen at 70° C for 3 hours. After washing twice with a sodium metabisulfite solution and with water, the reaction mixture was dried and concentrated to a small volume. After treating the residue with hexane, 1.2 g of crude material was isolated which was purified with column chromatography [silica gel, 10:1 (v/v) methylene chloride ethyl acetate] to obtain 0.33 g (0.5 mmole; 23% yield) of 1-(1-p-nitrobenzyloxycarbonyl-2-bromomethylprop-2-enyl)-3-phenoxyacetamido-4-phthalimidothioazetidin-2-one.

Provenance & Evidence