Isopropanol → HCID 57025855, compound

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Reaction Steps

To a solution of 0.323 g of 8 in 10 ml of acetone there is added 0.77 ml ofa solution that is 3.25 molar in chromium trioxide and 5.29 molar in sulphuric acid. The mixture is stirred at room temperature for 40 minutes and then there are added 2 ml of isopropanol followed by 50 ml of ethyl acetate. 0.1 g of activated carbon is then added to the mixture. After 10 minutes, the mixture is filtered and washed with 50 ml of ethyl acetate. The filtrate is extracted three times with 50 ml of 10% sodium hydrogen carbonate solution each time. The aqueous phase is extracted twice with 40ml of ethyl acetate each time, acidified to pH 1 using 2N hydrochloric acid, and then extracted three times with 70 ml of ethyl acetate each time. The organic extracts are washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation. Chromatography on 8 g of silica gel using chloroform/methanol/acetic acid 18:1:1 as eluant yields 65 mg of 9. 1H-NMR (300 MHz, DMSO-d6): 1.37 (s, (CH3)3CO); 1.82 (d, J=2, CH3 --C(4)); 2.63 (d, J=22, 2H--C(5)); 3.61 (d, J=11, (CH3O)2PO); 4.62 (t, J=8, H--C(2)); 5.25 (m, H--C(3)); 7.18 (d, J=8, NH); 11.7-12.5 (CO2H).

Provenance & Evidence