Water → HCID 117857852, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.4 ml (43.9 mmol, 10 eq.) of trifluoroacetic acid and 0.33 ml water was cooled to −5° C. At this temperature, 1.88 g (6.59 mmol, 1.5 eq.) of ethyl (1E)-N-[(mesitylsulphonyl)oxy]ethanimidoate [CAS No: 38202-27-6] were added in portions. After 1.5 h, 30 ml of ice-water were added, the mixture was stirred briefly, and the precipitated O-(2-mesitylenesulphonyl)hydroxylamine (MSH) was filtered off by means of a precooled frit and washed with 30 ml of ice-water. The water-moist O-(2-mesitylenesulphonyl)hydroxylamine was dissolved in 12 ml of dichloromethane, dried with magnesium sulphate and filtered, and the filtrate was added dropwise directly to a solution of 1.03 g (4.39 mmol, 1.0 eq.) of 2-[(2,6-difluorobenzyl)oxy]-4-methylpyridine from Example 1A in 2 ml of dichloromethane. The mixture was stirred at RT overnight. Subsequently, diethyl ether was added dropwise, and the precipitate obtained was filtered off, washed with diethyl ether and dried. 1.3 g of the title compound were isolated (59% of theory, 90% purity).

Provenance & Evidence