(Diethylamino)sulfur trifluoride → HCID 22916662, compound

Participants

Reaction Steps

To a solution of 1.0 g of the above-obtained 2-(tert-butoxycarbonylamino)methyl-4-hydroxymethylthiazole in 20 ml of dichloromethane was added 0.6 ml of diethylaminosulphur trifluoride with ice-cooling, and the mixture was stirred at room temperature for 30 minutes. To this reaction solution was added 20 ml of a saturated aqueous solution of sodium hydrogencarbonate, and the mixture was stirred for 10 minutes. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (10 ml×2). The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with a 50:1 mixture of chloroform and methanol to give 0.535 g (yield 47%) of the title compound.

Provenance & Evidence