Triacetoxyperiodinane → 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilide

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Reaction Steps

A mixture of 360 mg (0.92 mmol) of 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2(RS)-hydroxy-2′,4′-dimethylvaleranilide and 424 mg (1 mmol) of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one in 10 ml of dichloromethane was stirred under a nitrogen atmosphere for 1 hour. The solution was extracted with a solution of 2.5 g of sodium thiosulphate in 10 ml of saturated sodium bicarbonate solution, then dried over anhydrous magnesium sulphate, filtered and evaporated to dryness. The residue was chromatographed on silica gel using 25% ethyl acetate in petroleum ether for the elution. The solid obtained was triturated with petroleum ether to give 222 mg of 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2′,4′-dimethyl-2-oxovaleranilide as a white solid, 1H NMR (250 MHz, CDCl3) δ:1.4 (s,9H), 2.25 (s,3H), 2.3 (s,3H), 2.8-3.1 (m,2H), 5.2-5.3 (m,1H), 5.4-5.5 (d,1H), 7.0-7.1 (m,2H), 7.7-7.8 (d,1H), 8.4-8.5 (br.s,1H).

Provenance & Evidence