Tetrabutylammonium Hydroxide → Tetrabutylammonium benzyl adipate

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Reaction Steps

To 11.8 g (0.05 mole) benzyl adipate half ester in 250 ml chloroform and 40 ml water is added 40% aqueous tetrabutylammonium hydroxide with vigorous stirring until the mixture is pH 8.5. The organic phase is separated, the aqueous layer extracted with chloroform and the combined extracts dried over anhydrous sodium sulfate. Evaporation of solvent gives tetrabutylammonium benzyl adipate as an oil. The oil is mixed with toluene (250 ml) and 2.56 g (0.05 mole) iodomethyl 6-[D-(2-azido-2-phenylacetamido)]-penicillanate is added. The mixture is stirred for one hour, diluted to 500 ml with ethyl acetate and the precipitated tetrabutylammonium iodide removed by filtration, washing with ethyl acetate. The filtrate and washings are washed with sodium bicarbonate solution, water, brine and dried (Na2SO4). Evaporation of solvent affords the title compound which is purified by silica gel chromatography.

Provenance & Evidence