Methanol → Silver benzoate

Participants

Reaction Steps

A solution of silver benzoate (1.0 g) and triethylamine (20 ml) was prepared. To a stirring mixture of (R)-3-diazo-2-oxo-1-(phenylmethyl)carbamic acid, 1,1-dimethylethyl ester (10.0 g, 34.56 mmol) and methanol (100 ml) was added a portion of the silver benzoate/triethylamine solution (10 ml). After 20 minutes additional silver benzoate/triethylamine was added (5 ml) and stirring continued for 45 minutes. The dark reaction mixture was treated with Celite, decolorizing carbon and brine. The resulting mixture was filtered through Celite and the filtrate concentrated, diluted with ethyl acetate and washed with water (twice), 1N sodium bicarbonate (twice), 1N hydrochloric acid (twice), 1N sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated to an amber oil. The oil was chromatographed (flash, silica gel LPS-1, benzene:isopropyl ether 85:15) to yield a colorless oil. The oil was triturated with hexane to yield the title compound as a colorless solid: 8.43 g (28.7 mmol); Rf =0.26 (silica gel, benzene:isopropyl ether 85:15).

Provenance & Evidence