Hexane → 7-[2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyimino-acetylamino]-3-formyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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Reaction Steps

2.2 (via MnO2): To a solution of 10.00 g (12.36 mMol) 7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-trityloxyimino-acetylamino]-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester in 100 ml tetrahydofurane and 100 ml dichloromethane is added in 13 portions in 15 min intervals 65 g manganese dioxide (0.75 Mol) with stirring. To the resulting suspension is added 10.0 g active coal and 500 ml ethyl acetate. The mixture is concentrated to a volume of 200 ml. To resulting suspension is added 100 ml n hexane and the mixture is purified by chromatography over 500 g silica gel using 1:2 mixture of n hexane: ethyl acetate as eluent. The product fraction are collected and evaporated to dryness under aspirator vacuum. The resulting foam is triturated with 30 ml t-butylmethyl ether to give 5.2 g of the title compound as a yellowish powder with identical analytical characteristics as in example 2.1.

Provenance & Evidence