Methanol → Silver benzoate

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).

1. customThe dark reaction mixture
2. additionwas treated with Celite
3. filtrationThe resulting mixture was filtered through Celite
4. concentrationthe filtrate concentrated
5. additiondiluted with ethyl acetate
6. washwashed with water (twice), 1N sodium bicarbonate (twice), 1N hydrochloric acid (twice), 1N sodium bicarbonate and brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated to an amber oil
9. customThe oil was chromatographed (flash, silica gel LPS-1, benzene:isopropyl ether 85:15)
10. customto yield a colorless oil
11. customThe oil was triturated with hexane

ORD record

ord-91cbe0da24d848c1bf43813699fbf010

Source dataset

uspto-grants-1988_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04720585