1,1-Dimethylethyl (((2,4,6-trimethylphenyl)sulphonyl)oxy)carbamate → HCID 18376035, compound

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Reaction Steps

Solid t-butoxycarbonyl-O-mesitylenesulfonylhydroxylamine (13.0 g 41.8 mmol)1 was added portionwise with stirring to TFA (40 ml) over 10 min then stirred for a further 30 minutes. The solution was poured onto ice (250 ml) and left until the ice melted. The resulting white solid was filtered off, washed with water, and dissolved in DCM (300 ml). The solution was dried over 4 Å mol. sieves for 1.5 hours, filtered and 6-[2-(4-fluorophenyl)-2-oxoethyl]nicotinonitrile (3.32 g 13.8 mmol) was added. The reaction was stirred at room temperature for 4 days, washed with water (100 ml), dried and purified by column chromatography. Elution with cyclohexane/ethyl acetate (3:1) gave the title compound as a yellow solid (0.6 g 18%). NMR: (CDCl3): δ 6.87 (1H, s) 7.15-7.20 (3H, m) 7.57 (1H, dd) 7.95 (2H, m) 8.84 (1H, d). Ref 1 Josef G Krause, Synthesis, 1972, 140.

Provenance & Evidence