Ethyl Acetate → HCID 13754459, compound

Participants

Reaction Conditions

Reaction Steps

N-(Benzyloxy)-N2 -(t-butoxycarbonyl)-α-(4-hydroxy-2,3,5,6-tetrahydro-4-pyranyl)glycinamide (1.9 g, 5 mmoles) in 20 ml of dry pyridine under argon was treated with 1.05 g (6.5 mmoles) of pyridine-sulfur trioxide and heated to 57° C. for 2 hours. The volatiles were removed in vacuo. Dry acetonitrile was added and evaporated four times, and the residue was treated with a solution of 5 g (36 mmole) of potassium carbonate in 12.5 ml of water, followed by 40 ml of ethyl acetate. The mixture was heated to reflux with vigorous stirring for 6 hours. The mixture was cooled, diluted with water, and the layers separated. The organics were washed with 3% potassium bisulfate and brine, dried (sodium sulfate) and evaporated to a solid. Chromatography on 350 ml of LPS-1 in hexane:ethyl acetate (1:1) and evaporation of the pure product fractions (Rf=0.56 in same solvent) gave a solid. Trituration with isopropyl ether and air drying gave the product as a white solid, 0.78 g, melting point 144°-146° C.

Provenance & Evidence